Category: 4584-49-0

Geetanjali, Y. published the artcileFurano compounds: synthesis of aroylbenzofurans, benzo[1,2-b:5,4-b’]difurans and their basic ethers, Product Details of C5H13Cl2N, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1985), 24B(11), 1129-32, database is CAplus.

Alkylaminoalkoxybenzofurans I (R = CH₂CH₂NR¹R², CHMeCH₂NMe₂, 3-piperidinopropyl; NR¹R² = NMe₂, NEt₂, pyrrolidino, piperidino, morpholino) have been synthesized by condensing I (R = H) with RCl.HCl in the presence of K₂CO₃ in dry Me₂CO. I (R = H) was obtained by refluxing 1,3-Ac₂C₆H₂(OH)₂-4,6 with BrCH₂Bz. Dibenzoylbenzo[1,2-b:5,4-b‘]difurans II (R³ = H, OMe, OH, OR) have also been synthesized. Condensation of BrCH₂Bz with 5-acetyl-6-hydroxy-2,3-diphenylbenzofuran results in 6-benzoyl-5-methyl-2,3-diphenylbenzo[1,2-b:5,4-b‘]difuran.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, Product Details of C5H13Cl2N.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Gupta, Atul published the artcileSynthesis of 3-phenyl-4-phenylvinylbenzopyranones and the corresponding 2,2-dimethylbenzopyrans with structural similarity to estradiol, as estrogen receptor ligands, Application of 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, the publication is Medicinal Chemistry (2007), 3(5), 446-454, database is CAplus and MEDLINE.

7-Methoxy-3-phenyl-4-phenylvinylbenzopyran-2-ones I [R¹R² = oxo, R⁴ = (CH₂)₂R⁵, CH(Me)CH₂NMe₂, R⁵ = 1-pyrrolidinyl, 1-piperidinyl, NMe₂, NEt₂] and the corresponding 2,2-dimethylbenzopyrans I [R¹ = R² = Me] substituted with different alkylamino residues were synthesized. Except compound I [R¹R² = oxo, R⁴ = CH(Me)CH₂NMe₂], all compounds showed high levels of estrogen agonistic activity (>81 %) whereas, compounds I [R¹R² = oxo, R⁴ = (CH₂)₂R⁵, CH(Me)CH₂NMe₂, R⁵ = 1-piperidinyl, NMe₂, NEt₂] and I [R¹ = R² = Me, R⁴ = (CH₂)₂R⁵, R⁵ = 1-pyrrolidinyl] showed significant estrogen antagonistic activity (>20 %). X-Ray anal. of I [R¹R² = oxo, R⁴ = (CH₂)₂NEt₂] showed its structural resemblance to endogenous estrogen, 17β-estradiol. Estrogenic and anti-estrogenic activities of these derivatives demonstrate their estrogen receptor (ER) binding ability. The lack of hydroxyl groups at appropriate positions resulted in poor relative binding affinity (RBA).

Medicinal Chemistry published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, Application of 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Cai, Xing-wei published the artcileLead/rare earth-free green-light-emitting crystal of molecular-based hybrid compound: (C₅H₁₃ClN)₂[MnCl₄] with large crystal size, COA of Formula: C5H13Cl2N, the publication is Wuji Huaxue Xuebao (2018), 34(2), 283-288, database is CAplus.

Reaction of MnCl₂ and 2-dimethylaminoisopropyl chloride hydrochloride afforded one novel mol.-based material, (C₅H₁₃ClN)₂[MnCl₄] (1). And it is interesting to note that 1 exhibits intense greenish fluorescent emission (520 nm) at room temperature and relatively high thermal stability (stable up to 450 K). Moreover, structure and spectra analyses reveal that its excellent optical property can be attributed to the ⁴T₁ (G) → ⁶A₁ electronic transition of Mn²⁺ in [MnX₄]^2- tetrahedron.

Wuji Huaxue Xuebao published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, COA of Formula: C5H13Cl2N.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Brzozowski, Zdzislaw published the artcileDerivatives of 2-mercaptobenzenesulfonamide. XIII. Syntheses and some pharmacological properties of 1-[4-chloro-2-(dialkylaminoalkylthio)-5-methylbenzenesulfonyl]-2-imidazolidinone hydrochlorides, COA of Formula: C5H13Cl2N, the publication is Acta Poloniae Pharmaceutica (1993), 50(4-5), 359-64, database is CAplus and MEDLINE.

In the search for new antiarrhythmic agents, 3-[(4-chloro-2-mercapto-5-methylphenyl)sulfonyl]imidazolidinone I (R = H) was treated with dialkylaminoalkyl chloride hydrochlorides in Me₂CHONa-Me₂CHOH to yield I (R = Me₂NCH₂CHMe, Me₂NCMe₂CH₂, and R¹CH₂CH₂; R¹ = Pr₂N, Bu₂N, (C₆H₁₁)₂N, piperidinyl, 2,6-dimethylpiperidinyl, morpholinyl, and piperazinyl). Data for LD₅₀ and activity against acinitine- and BaCl₂-induced arrhythmia in rats are presented for I hydrochlorides.

Acta Poloniae Pharmaceutica published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, COA of Formula: C5H13Cl2N.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Rhee, Hee-Kyung published the artcileSynthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones, Application In Synthesis of 4584-49-0, the publication is Bioorganic & Medicinal Chemistry (2007), 15(4), 1651-1658, database is CAplus and MEDLINE.

Benzofuroquinolinediones (7c and 7d) were synthesized by base-catalyzed condensation of dichloroquinolinediones with phenolic derivatives Their dialkylaminoalkoxy derivatives (8i-8p) were prepared by reaction with various dialkylaminoalkyl chlorides. The cytotoxicity of the synthesized compounds was evaluated against eight types of human cancer cell lines, and their topoisomerase II inhibition was assessed. In general, the cytotoxicity of benzofuroquinolinediones (8i-8p) was similar or superior to that of doxorubicin and showed more potent inhibitory activity than naphthofurandiones (8a-8h). Also, most of the compounds exhibited excellent topoisomerase II inhibitory activity at a concentration of 5 μM and two compounds, 8d and 8i, showed IC₅₀ values of 1.19 and 0.68 μM, resp., and were much more potent than etoposide (IC₅₀ = 78.4 μM), but similar to doxorubicin (IC₅₀ = 2.67 μM). However their inhibitory activity on topoisomerase I was lower, and 8d and 8i showed IC₅₀ values of 42.0 and 64.3 μM, resp.

Bioorganic & Medicinal Chemistry published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, Application In Synthesis of 4584-49-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Walton, E. published the artcileNew analgesics. III. Homologs of amidone, isoamidone, and some related compounds, Product Details of C5H13Cl2N, the publication is Journal of the Chemical Society (1949), 648-55, database is CAplus.

cf. C.A. 42, 6814d. In view of the established value of amidone (Me₂NCHMeCH₂CPh₂COEt) as an analgesic, 4 series of related ketones have been prepared by condensing Ph₂CHCN with a Cl base and treating the resulting basic cyanides with Grignard reagents. In general, the analgesic and respiratory depression activities remain associated but not always in the same ratio, maximum activity being attained in the Et ketone in all 4 series. Data are given for the analgesic activity, respiratory depression activity, approx. LD₅₀ (i.v. injection into mice), and toxic concentration on isolated rabbit heart. MeCH(NMe₂)CH₂OH (32 g.) and 46 mL. SOCl₂ in 120 mL. CHCl₃, warmed 3 h., give 1-chloro-2-(dimethylamino)propane-HCl, deliquescent, m. 101-2°; heated 3 min. at 140-60°, it yields MeCHClCH₂NMe₂.HCl (not changed by heating at 190-200°), which results also from MeCH(OH)CH₂NMe₂ and SOCl₂. A mixture of 26 g. Me₂NCHMeCH₂CPh₂CN (I) and Me₂NCH₂CHMeCPh₂CN (II) (prepared by the German process, Rept. Number P.B. 981, Office of the Pub. Board, Wash., D. C., p. 84) crystallized from petr. ether (b. 60-80°), gives 13.5 g. I, m. 90-1° (HCl salt, m. 181-3°; HBr salt, m. 175°; HI salt, cream, m. 203-4°; nitrate, m. 168-70° (decomposition); methiodide, m. 238-46°); the oil from the mother liquor of I, treated with 40% HBr, gives 14 g. of the HBr salt, m. 223-4°, of II, m. 68-9°; HCl salt, m. 224-5°; HI salt, m. 212-13°; nitrate, m. 178° (decomposition); H D-tartrate, m. 88-98°; methiodide, m. 235-45°. I (5 g.) in 20 mL. xylene and MeMgI (7.7 g. MeI), heated 2 h. on the steam bath (ether allowed to evaporate) and 2 h. on a sand bath, give 5-dimethylamino-3,3-diphenyl-2-hexanone, m. 72-3° (HCl salt, m. 185-7°; HBr salt, m. 193-5°; HI salt, m. 180-2°). Amidone (III) (m. 80-2°) yields a HI salt, m. 198-9°, a nitrate m. 108-10° (decomposition), and a methiodide, m. 168-70°. I and PrMgI give 7-dimethylamino-5,5-diphenyl-4-octanone which yields a nitrate, m. 95-7°, a HI salt, m. 155-7°, and a HBr salt, m. 87-9°. I and iso-PrMgBr give 6-dimethylamino-4,4-diphenyl-2-methyl-3-heptanone, b₄ 176-86° (nitrate, m. 116-18°). I and BuMgI yield 2-dimethylamino-4,4-diphenyl-5-nonanone, characterized as the HCl salt, m. 83-6°; HBr salt, m. 103-5°; HI salt, m. 140-3°, and nitrate, m. 77-8°. I and PhMgBr give the intermediate ketimine (C₂₅H₂₈N₂.HCl), m. 136-8°; refluxed 2 h. with 20% HBr, this yields the HBr salt, m. 181-3°, of Ph 3-dimethylamino-1,1-diphenylbutyl ketone; HCl salt, m. 197-8°. I and PhCH₂MgBr give 5-dimethylamino-1,3,3-triphenyl-2-hexanone-HCl, m. 236-7°; HBr salt, m. 243-4°. I (40 g.) and 21.6 g. D-tartaric acid in 430 mL. Me₂CO and 10 mL. H₂O, kept 24 h. at 0°, give 28 g. of the H D-tartrate, m. 109-12°, [α]_D²⁰ 16° (H₂O), of (-)-I, m. 99-101°, [α]_D²¹ -51° (EtOH); the Me₂CO mother liquors plus a little ether, kept 4 days at 0°, give 14 g. of the H D-tartrate, m. 66-70°, [α]_D²⁰ 5° (H₂O), of (+)-I, m. 101°, [α]_D²² 49° (EtOH); HBr salt, m. 216-18°, [α]_D²² 5 (EtOH), -4° (H₂O); nitrate, m. 169-71° (decomposition), [α]_D²⁰ 5° (EtOH), -6° (H₂O). (-)-I and EtMgBr give (-)-III, m. 99-101°, [α]_D²² -32° (EtOH); HBr salt, m. 234-5°, [α]_D²² -134° (EtOH); HCl salt, m. 241-2° (decomposition), [α]_D²¹ -130° (H₂O). (+)-III, m. 98-100°, [α]_D²⁰ 28° (EtOH); HI salt, m. 175-7° (decomposition); nitrate, m. 148° (decomposition), [α]_D¹⁹ 137° (EtOH). I (2 g.), 4 mL. concentrated H₂SO₄, and 4 mL. H₂O, refluxed 20 min., give 2.3 g. of the acid sulfate, m. 222-3°, of γ-dimethylamino-α,α-diphenylvaleric acid (IV), m. 198-9° (decomposition); HCl salt, m. 213-16°; the mother liquor yields the amide, m. 175-6° (HCl salt, m. 190-1°); Me ester, m. 60-5° [HCl salt, m. 166-8° (decomposition); HBr salt, m. 182° (decomposition)]; Et ester, an oil (HBr salt, m. 167-8°). I (5 g.), 0.7 g. NaNH₂, and 10 mL. PhMe, refluxed 6-7 h., give 2.5 g. I and 3-dimethylamino-1,1-diphenylbutane, whose HBr salt m. 159-60°; it results also on heating IV 15 min. at 200°; methiodide, m. 195-6°. IV (0.8 g.) and 0.5 mL. SOCl₂ in CHCl₃, warmed 4 h. on the steam bath, give 3,3-diphenyl-1,5-dimethyl-2-pyrrolidone, m. 122-3°. II and MeMgI in xylene, heated 1 h. on the steam bath and refluxed 1 h., give the ketimine (methiodide, C₂₁H₂₉N₂I, decompose 176-230°), which yields 5-dimethylamino-3,3-diphenyl-4-methyl-2-pentanone, m. 61-5° (HBr salt, m. 194-6°). II (16.6 g.) and EtMgBr give the ketimine, b₁ 94° (methiodide, m. 240°); refluxed 2.5 h. with 20% HBr, it yields 10.3 g. 6-dimethylamino-4,4-diphenyl-5-methyl-3-hexanone-HBr, m. 139-44°; HI salt, m. 206-8°; nitrate, m. 182-3° (decomposition); H D-tartrate, m. 150-4°. II (16.6 g.) and PrMgBr give 3.75 g. of the HCl salt, m. 80-100°, of 1-dimethylamino-3,3-diphenyl-2-methyl-4-heptanone, m. 100-1°. II and 5 mols. iso-PrMgBr give 6-dimethylamino-4,4-diphenyl-2,5-dimethyl-3-hexanone, whose HBr salt m. 81-5°. II and excess 48% HBr, heated 3.5 h. at 180°, give 3,3-diphenyl-1,4-dimethyl-2-pyrrolidone, m. 121-3°. Ph₂CHCN (67.2 g.), 22 g. Me₂N(CH₂)₂CN, and 6.8 g. NaNH₂ in 200 mL. C₆H₆ give 39 g. crude 3-dimethylamino-1,1-diphenylpropyl cyanide (V); HCl salt, m. 196-7°; HI salt, m. 221-3°. V (14 g.) gives 9 g. 5-dimethylamino-3,3-diphenyl-2-pentanone (HCl salt, m. 152-3°); EtMgBr gives 6-dimethylamino-4,4-diphenyl-3-hexanone (HCl salt, m. 171-2°); PrMgI gives 1-dimethylamino-3,3-diphenyl-4-heptanone (HI salt, m. 156-7°); iso-PrMgBr yields 6-dimethylamino-4,4-diphenyl-2-methyl-3-hexanone (HBr salt, m. 104-6°). 3-(1-Piperidyl)-1,1-diphenylpropyl cyanide (VI), m. 73-4° [HCl salt, m. 196-7°; HBr salt, m. 185-6°; HI salt, m. 152-3°; nitrate, m. 155° (decomposition)]. VI and MeMgI give 5-(1-piperidyl)-3,3-diphenyl-2-pentanone (HBr salt, m. 162-3°; HI salt, m. 158-9°); EtMgI yields 6-(1-piperidyl)-4,4-diphenyl-3-hexanone (HBr salt, m. 192-3°); PrMgI gives 1-(1-piperidyl)-3,3-diphenyl-4-heptanone (HCl salt, m. 158-60°; HI salt, m. 217-20°). VI and PhMgBr give Ph 3-(1-piperidyl)-1,1-diphenylpropyl ketone-HBr, m. 191-3°. VI (1.9 g.) and 3.6 mL. H₂SO₄, refluxed 30 min., give 0.5 g. α,α-diphenyl-1-piperidinebutyric acid, m. 230-5° (decomposition) (HCl salt, m. 236° (decomposition); H sulfate, m. 105-14°), and 0.6 g. of the amide, m. 178-9°; Me ester-HBr, with 2 mols. H₂O, m. 78-82°; Et ester-HBr, m. 194-6°. VI (2.3 g.), 0.9 g. NaNH₂, and 25 mL. C₆H₆, refluxed 3 h., give 3-(1-piperidyl)-1,1-diphenylpropane-HCl, m. 208-10°.

Journal of the Chemical Society published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C4H6O3, Product Details of C5H13Cl2N.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Geethanjali, Y. published the artcileSynthesis and antimicrobial activity of 7-(β-t-alkylaminoalkoxy)-8-benzoyl-4-methyl coumarins, Synthetic Route of 4584-49-0, the publication is Indian Journal of Heterocyclic Chemistry (1995), 4(4), 307-8, database is CAplus.

Title compounds were prepared by reaction of 7-hydroxy-8-benzoyl-4-methylcoumarin with various alkylaminoalkyl chloride hydrochlorides and were screened for antimicrobial activity. 7-(3-Piperidinopropoxy)-8-benzoyl-4-methylcoumarin showed marked antifungal and antibacterial activity.

Indian Journal of Heterocyclic Chemistry published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, Synthetic Route of 4584-49-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wan, Zhongliang published the artcileSynthesis and Biological Activity of 3-N-Substituted Estrogen Derivatives as Breast Cancer Agents, Product Details of C5H13Cl2N, the publication is Mini-Reviews in Medicinal Chemistry (2013), 13(9), 1381-1388, database is CAplus and MEDLINE.

3-N-substituted-estrogen derivatives I [R = 3-morpholinopropyl, (CH₂)₃NMe₂, CH(Me)CH₂NMe₂, 3-piperidinopropyl, 3-aminopropyl, etc.] were synthesized and characterized. Their antiproliferative activities against human ER(+) MCF-7 (breast), ER(-) MDA-MB-231 (breast) and Ishikawa (endometrial) cancer cell lines were determined after 72 h drug exposure employing CellTiter-Glo assay at concentrations ranging from (0.01-100,000 nM). The antiproliferative activities of these compounds were compared to tamoxifen (TAM), 4-hydroxytamoxifen (4-OHT, active metabolite of tamoxifen) and raloxifene (RAL). In vitro results indicated that compound I (R = 3-piperidinopropyl) (IC₅₀ = 12μM) displayed comparable antiproliferative activity against MDA-MB 231 cell line; while compounds I [R = (CH₂)₃NMe₂, CH(Me)CH₂NMe₂, (CH₃)₃NEt₂] (IC₅₀ = 12μM) displayed higher activity against MCF-7 and Ishikawa cell lines, in comparison to TAM activity (19-33μM).

Mini-Reviews in Medicinal Chemistry published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C13H17BrO3, Product Details of C5H13Cl2N.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Galons, Herve published the artcileA convenient procedure for the synthesis of phenothiazine drugs, Related Products of chlorides-buliding-blocks, the publication is Chemical & Pharmaceutical Bulletin (1985), 33(11), 5108-9, database is CAplus.

Alkylation of phenothiazines to prepare chloropromazine and analogous compounds was achieved by solid-liquid phase-transfer catalysis in the presence of Aliquat 336 in the absence of any organic solvent. This simple procedure is easy and rapid.

Chemical & Pharmaceutical Bulletin published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, Related Products of chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Marquina, J. G. published the artcileDerivatives of N-methyl-4-phenylpiperidine-4-carboxylic acid and 2,2-diphenyl-4-dimethylaminovaleric acid, COA of Formula: C5H13Cl2N, the publication is Farm. Nueva (Madrid) (1961), 381-92, database is CAplus.

Methylbis(2-hydroxyethyl)amine (75 g.) in 75 ml. anhydrous C₆H₆ was added slowly with stirring to 125 mi. SOCl₂ in 75 ml. C₆H₆ below 50° the mixture heated 2 hrs. at 50-5°, SOCl₂ removed in vacuo on a water bath, alc. added, the solution concentrated, and the solid crystallized from 500 ml. Me₂CO to give 72 g. methylbis(2-chloroethyl)amine-HCl (I), m. 110°; picrate, m. 133°. To 70.2 g. PhCH₂CN and 115.2 g. I in 400 ml. C₆H₆ at 30-40° was added slowly with stirring 100 g. NaNH₂, the mixture refluxed 2 hrs., diluted with H₂O and extracted with HCl, the solution made alk. and extracted with Et₂O, and the extract distilled in vacuo to give 63 g. N-methyl-4-phenylpiperidine-4-nitrile (II), b₄ 148°, m. 53°; HCl salt m. 221-2°. A mixture of 478 g. II, 637 g. H₂SO₄, and 155 ml. H₂O was heated 1 hr. at 145-50°, cooled and treated with NH₃ to pH 7-8 and the solid filtered off and washed to give 330 g. N-methyl-4-phenylpiperidine-4-carboxylic acid (III), m. 301-2° (H₂O). To 27 g. III was added slowly 40 ml. SOCl₂, the mixture heated 1 hr. on a water bath, 100 ml. C₆H₆ was added, the mixture allowed to crystallize, the solution filtered, and the solid washed with C₆HO and petr. ether to give 27.5 g. III acid chloride (IV), which was used immediately. NaCN (25 g.) in 90 ml. H₂O was added slowly with stirring to 100 ml. H₂O containing 100 g. BzH bisulfate. the solution extracted with C₆H₆, the dry extract added slowly with stirring to 200 ml. C₆H₆ containing 135 g. AlCl₃ at 8 10° and the mixture kept 1 day then heated 1 hr. at 80° washed with H₂O and distilled in vacuo to give 67 g. diphenylacetonitrile (V), b_1-2 122-5°, m. 69-70°. SOCl₂ (67 g.) in 100 ml. C₆H₆ was added to 50 g. 1-dimethylamino-2-propanol in 100 ml. C₆H₆ at 20-5°, the solution refluxed 2 hrs., cooled, and the mixture filtered, and the solid recrystallized to give 60 g. 2-chloro-1-dimethylaminopropane-HCl (VI.HCl), m. 185-6°. To 72 g. V and 55 g. pulverized NaOH was added 90 g. VI in Et₂O, the Et_O distilled, the mixture heated to 95-100° with stirring for 10 hrs., washed with H₂O, treated with anhydrous HCl, rehydrolyzed, and distilled in vacuo to give 45 g. 2,2-diphenyl-4-dimethylaminovaleronitrile (VII), b_1-2 180-4°, m. 91° (petr. ether). To 600 g. VII was added 650 ml. H₂SO₄ in 420 ml. H₂O, the solution heated 5 hrs. at 150°, cooled and filtered to give 570 g. 2,2-diphenyl-4-dimethylaminovaleric acid-H₂SO₄ (VIII.H₂SO₄), m. 224-6° (H₂O). To 40 g. VIII was added 40 ml. SOCl₂, and the mixture refluxed 1 hr. on a steam bath, treated with 100 mi. C₆H₆, cooled, allowed to crystallize, filtered, and washed with C₆H₆-petr. ether to give 41.5 g. VIII acid chloride (IX) which was used immediately. Et carbamate (17.8 g.) in 250 ml. C₆H₆ was added with stirring to 10 g. 50% NaH in mineral oil in 150 ml. C₆H₆ at 6-7°, and the mixture stirred 30 min., treated slowly with 24.7 g. III in 150 ml. C₆H₆ at 6-7°, stirred 2 hrs., then 4 hrs. at ambient temperature, extracted with 5% HCl, treated with Na₂CO₃, extracted with C₆H₆, and distilled in vacuo to give 7 g. N-methyl-4-phenylpiperidine-4-carboxyethyl carbamate (X), m. 140-1.5 (Me₂CO). Similarly, the following esters of III were prepared (alkyl carbamate and m.p. given): Pr, 138-9.5°; iso-Pr, 136-8°; allyl, 112-13.5°; Bu, 99.5-100.5° (picrate m. 163-4.5°; HCl salt m. 108-10°). Et carbamate (26.7 g.) in 300 ml. C₆H₆ was added with stirring to 6.9 g. finely divided Na in 150 ml. C₆H₆ at 6-7% and the mixture stirred 30 min., treated slowly at 6-7° with 41.4 g. IX suspended in 150 ml. C₆H₆, stirred 2 hrs. at 6-7° then 4 hrs. at ambient temperature, washed with H₂O, extracted with 5% HCl, and treated with Na₂CO₃ to give 10 g. Me₂NCHMe CH₂CPh₂CONHCO₂Et, m. 153-4.5° (Me₂CO). Similarly were prepared the following esters of VIII (alkyl carbamate, m.p. given): Pr, 158-9°; iso-Pr, 140-1°; allyl, 139-9.5°; Bu, 97-7.5° picrate, m. ∼128°. Analgesic activity was nil for derivatives of VI and VIII. Spasmolytic activity was slight for derivatives of VI, but high for derivatives of VIII.

Farm. Nueva (Madrid) published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, COA of Formula: C5H13Cl2N.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics