26487-67-2 Archives - Page 2 of 4 - Chlorides-buliding-blocks

Share a compound : 1-(2-Chloroethyl)azepane hydrochloride

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Chloroethyl)azepane hydrochloride, and friends who are interested can also refer to it.

Application of 26487-67-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 26487-67-2 name is 1-(2-Chloroethyl)azepane hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 12 11-Cyano-11-[2(hexamethyleneimino)ethyl]-6,11-dihydrodibenz[b,e]oxepin oxalate To a solution of 11-cyano-6,11-dihydrodibenz[b,e]oxepin of Example 1A (7.2 g; 0.032 mole) in dry DMF (110 ml) at 5° C. is added sodium hydride (1.9 g; 0.08 mole) portionwise under a nitrogen atmosphere. After stirring at ambient temperature for 11/2 hours, the reaction is cooled to 10° C. and 2-(hexamethylene-imino)ethyl chloride hydrochloride (6.9 g; 0.035 mole) is added portionwise. Stirring is continued at 100° C. for 21/2 hours. The reaction is cooled and poured into two liters of ice water, extracted with ether and the ether back extracted with 2 N HCl. The acidic extracts are combined and made basic with sodium hydroxide. After extracting with ether, washing with a saturated NaCl solution and drying (K2 CO3), the ether is removed in vacuo to provide 3.0 g of an oil (27percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Chloroethyl)azepane hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Hoechst-Roussel Pharmaceuticals Inc.; US4335122; (1982); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Extended knowledge of C8H17Cl2N

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 1-(2-Chloroethyl)azepane hydrochloride

To a solution of 1,1-bis(4-hydroxyphenyl)but-1-ene (80.0 mg, 0.333 mmol) in DMF (3.33 mL) at 0 °C was added 60percent sodium hydride (dispersion in paraffin liquid, 79.9 mg, 2.00 mmol). The reaction mixture was stirred for 15 min at 50 °C and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (216 mg, 1.09 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 3 h at 50 °C, saturated aqueous ammonium chloride was added at 0 °C. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 9/1) to afford RID-F-S*2 (compound 22) (130 mg, 80percent) as an orange oil

Reference:
Article; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Simple exploration of 26487-67-2

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H17Cl2N

General procedure: Commercially available 5-chloro benzoxazoles or benzothiazoles(5 mmol) and K2CO3 (15 mmol) were added to 50 mL of DMF.The mixture was heated at 60 C and 1-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (6.5 mmol) was added. The mixture was maintained at 60 C under stirring for 3 h, then was cooled to room temperature, poured into water, and extracted with diethyl ether(3 50 mL). The organic layer was washed with brine, dried overan hydrous Na2SO4 and evaporated under reduced pressure to give are sidue, which was purified by flash column chromatography oversilica gel using ethyl acetate/methanol 8:2 v/v as eluent. Immediately after solvent evaporation, free bases were converted into hydrochlorides by dissolving the corresponding amine in diethyl ether and treating with a 1.25MHCl ethanol solution (pH 1e2). The precipitate was filtered off, washed with diethyl ether, and dried under nitrogen. The following compounds were obtained using this procedure:

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romeo, Giuseppe; Prezzavento, Orazio; Intagliata, Sebastiano; Pittala, Valeria; Modica, Maria N.; Marrazzo, Agostino; Turnaturi, Rita; Parenti, Carmela; Chiechio, Santina; Arena, Emanuela; Campisi, Agata; Sposito, Giovanni; Salerno, Loredana; European Journal of Medicinal Chemistry; vol. 174; (2019); p. 226 – 235;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

New downstream synthetic route of 26487-67-2

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

To a solution of 1,1-bis(4-hydroxyphenyl)ethane (50.0 mg, 0.233 mmol) in DMF (2.33 mL) at 0 °C was added 60percent sodium hydride (dispersion in paraffin liquid, 56.0 mg, 1.40 mmol). The reaction mixture was stirred for 15 min at 50 °C and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (153 mg, 0.772 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 23 h at 50 °C, saturated aqueous ammonium chloride was added at 0 °C. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 30/1) to afford RID-F-S*101 (compound 26) (93.9 mg, 87percent) asa pale yellow oil

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Brief introduction of 1-(2-Chloroethyl)azepane hydrochloride

Add sodium hydride (324 mg, 8.0 mmol) into a solution of 4- [6-benzyloxy-2- (4- fluoro-phenyl)-naphthalen-1-yloxy]-phenol (1.18 g, 2.7 mmol) in DMF (10 mL) and stir for 20 minutes at room temperature. Add 2- (hexamethyyleneimino) ethyl chloride hydrogen chloride (1.07 g, 5.4 mmol) and stir at room temperature for 12 hours. Add H20 (10 mL) and diethyl ether (100 mL). Separate layers and wash the aqueous layer with diethyl ether (2 x 50 mL). Combine organic layers, dry with magnesium sulfate and concentrate in vacuo. Purify the residue over silica gel, eluting the material with a step gradient of methanol/dichloromethane (0percent to 10percent), to obtain 1.0 g of the title compound (66percent): mass spectrum (ion spray) m/z=562.3 (M+H).

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Sources of common compounds: C8H17Cl2N

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

To a solution of 1,1-bis(4-hydroxyphenyl)cyclohexane (50.0 mg, 0.186 mmol) in DMF (1.86 mL) at 0 °C was added 60percent sodium hydride (dispersion in paraffin liquid, 44.7 mg, 1.12 mmol). The reaction mixture was stirred for 15 min at 50 °C and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (122 mg, 0.616 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 23 h at 50 °C, saturated aqueous ammonium chloride was added at 0 °C. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 9/1) to afford RID-F-S*103 (compound 29) (62.7 mg, 65percent) as an orange oil

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

A new synthetic route of C8H17Cl2N

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Application of 26487-67-2, A common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Add sodium hydride (18 g, 0.45 mol) into a solution of 4-benzyloxylphenol (41 g, 0.20 mol) and 2- (hexamethyleneimino) ethyl chloride hydrochloride (44 g, 0.22 mmol) in THF (600 mL) and DMF (100 mL) at room temperature. Heat to 60°C for 30 minutes. Pour the solution into ice and water. Dilute with ethyl acetate (500 mL) and separate layers. Dry the organic layer with magnesium sulfate, filter and concentrate under reduced pressure to give brown oil. Dissolve the oil in ethyl acetate (500 mL) and methanol (500 mL). Add ammonium formate (100 g, 1.59 mol) and palladium on carbon (10 g, 9.4 mmol). Heat the mixture to reflux for 30 minutes. Add ammonium formate (100 g, 1.59 mol) and palladium on carbon (10 g, 9.4 mmol). Heat the reaction mixture for 30 minutes. Filter the supension through a pad of celite and elute with ethyl acetate (500 mL). Evaporate solvent under reduced pressure and add water (100 mL). Dilute the mixture with ethyl acetate (500 mL) and separate layers. Wash the organic layer with saturated sodium bicarbonate solution (2 x 200 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to give 31 g (64 percent) of4- (2-azepan-l-yl- ethoxy)-phenol. Combine 2-benzyloxy-1-bromo-6-methoxy-naphthalene (31 g, 90 mmol), 4- (2- azepan-l-yl-ethoxy)-phenol (31 g, 132 mmol), copper bronze (12 g, 189 mmol), potassium carbonate (25 g, 181 mmol) and pyridine (400 mL). Heat the reaction mixture to reflux for 85 hours. Cool and filter the residue with celite and elute with methanol and methylene chloride (500 mL, Vu = 1 : 5). Evaporate solvent under reduced pressure and chromatograph the residue on a silica gel column eluting the material with a step gradient of methanol/dichloromethane (0 to 10percent) to get 19 g (43percent) of 1- {2- [4- (2-benzyloxy-6- meCoxy-naphthalen-l-yloxy)-phenoxyl-ethyl}-azepane. Dissolve 1- {2- [4- (2-benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}- azepane (19 g, 38 mmol) in ethyl acetate (500 mL) and methanol (600 mL). Heat the mixture to obtain a clear solution. Cool to room temperature. Add ammonium formate (30 g, 476 mmol) and palladium on carbon (2 g, 1. 9 mmol). Heat to reflux for 30 minutes. Add ammonium formate (7 g, 111 mmol) and palladium on carbon (0.7 g, 0.7 mmol). Heat to reflux for 30 minutes. Filter the supension through a pad of celite and elute with ethyl acetate (500 mL). Evaporate solvent under reduced pressure and add water (100 mL). Dilute the mixture with ethyl acetate (500 mL) and separate layers. Wash the organic layer with saturated sodium bicarbonate solution (2 x 200 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to give 15.1 g (97percent) of 1- [4- (2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-napbthalen-2-ol. Add trifluoromethanesulfonic anhydride (7 mL, 42 mmol) into a solution of 1- [4- (2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-naphthalen-2-ol (15 g, 37 mmol), triethylamine (20 mL) and methylene chloride (500 mL) at-50°C. Warm the reaction mixture to room temperature and stir for 1 hour at that temperature. Cool the reaction mixture to-78°C and add brine (20 mL). Warm the reaction to room temperature. Separate layer and wash the organic layer with saturated sodium bicarbonate solution (100 mL) and brine. Dry the organic layer with magnesium sulfate, filter and evaporate solvent under reduced pressure. Chromatograph the residue on a silica gel column eluting the material with a step gradient of methanol/dichloromethane (0 to 10percent) to get 20 g (99percent) of trifluoro-methanesulfonic acid 1- [4-(2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy- naphthalen-2-yl ester.

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The important role of 26487-67-2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26487-67-2, its application will become more common.

Some common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 1-(2-Chloroethyl)azepane hydrochloride

Example 7 1-(2-(1-Perhydroazepinyl)ethyl)-3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine A solution of 1-(2-chloroethyl)perhydroazepine hydrochloride (42 mg, 0.21 mmol) in N,N-dimethylformamide (1 mL) was treated with triethylamine (30 muL, 0.22 mmol) then transferred to a flask containing 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 45 mg, 0.176 mmol) in N,N-dimethylformamide (2 mL). Sodium iodide (32 mg, 0.21 mmol) and sodium hydrogencarbonate (18 mg, 0.21 mmol) were added and the resultant mixture was heated at 60¡ã C. overnight. The solvent was then removed in vacuo and the residue was partitioned between saturated aqueous sodium hydrogencarbonate solution (5 mL) and dichloromethane (5 mL). The phases were separated and the aqueous layer was further extracted with dichloromethane (2*5 mL). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by reversed phase preparative HPLC (condition 2) to give the acetate salt of the title compound. The free base was obtained by treating with dilute aqueous ammonia solution (2 mL) and extracting with ether (4*3 mL). Drying over Na2SO4, filtering and evaporation to dryness gave the title compound as a white solid (16 mg, 24percent). NMR (CDCl3, selected data for the free base): 0.8 (d, 3H), 1.35 (s, 3H), 1.6-1.8 (m, 9H), 2.10 (m, 1H), 2.4-2.5 (m, 2H), 2.6-3.0 (m, 11H), 7.25 (d, 1H), 7.35 (t, 1H), 7.55 (d, 1H), 7.85 (s, 1H), 7.95 (s, 1H). MS (thermospray): M/Z (MH+) 382.6; C23H35N5+H requires 382.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26487-67-2, its application will become more common.

Reference:
Patent; Gibson, Stephen Paul; Tommasini, Ivan; Verrier, Kimberley; Dutton, Christopher James; Gethin, David Morris; Critcher, Douglas James; Armer, Richard Edward; US2003/4340; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 26487-67-2

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(2-Chloroethyl)azepane hydrochloride, other downstream synthetic routes, hurry up and to see.

Electric Literature of 26487-67-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 27: Synthesis of (4-methoxyphenyI)(naphthalen-l-yl)methanone O- 2-(azepan-l-yl)ethyl oxime oxalate (Compound 6g). Into a 50 ml round bottom flask, 4-(methoxy phenyl (naphthalen-l-yl)methanone oxime (1 mmole, 277 mg), l-(2-Chloro-ethyl)-azepane hydrochloride (1.2 mmole, 237.6 mg), baked K2C03 (5 mmole, 690 mg) and dry acetone (10.0 ml) were taken. The reaction mixture was refluxed under anhydrous conditions for 6 hours. The reaction was followed by TLC monitoring. After completion of the reaction, K2C03 was filtered off and washed with acetone (2×10 ml). Filtrate was concentrated and the crude product was purified by basic alumina column chromatography using distilled Hexane to yield the pure product (312mg, 77.61percent). The product obtained was oily so a salt of the compound was prepared. Procedure for oxalate salt formation: Oxalic acid, 1 mmole/ 1 mmole of compound, (97.79 mg) and oily product (312 mg) were dissolved in dry methanol separately into two round bottom flasks. The acid and the compound were mixed and shaken thoroughly. The salt was precipitated using dry diethyl ether, filtered, washed with the same and collected. Yield: 331 mg, 62.69percent. MP. (Oxalate Salt of compound)= 122 ¡ãC; ESI MS(m/z)= 403 (M+H), I (KBr, Cm-1): 3446.5, 2933.9, 2599.9, 1721.6, 1607.9, 1510.2, 1459.5, 1251.3, 1 177.9, 1026.7, 960.1, 719.2; NMR (300MHz, CDC13): delta= 7.92(d, J=8.0 Hz, 2H, ArH), 7.69(d, J=8.2 Hz, 1H, ArH), 7.58-7.39(m, 5H, ArH), 7.33-7.28(m, 1H, ArH), 6.84(d, J=8.5 Hz, 2H, ArH), 4.27(t, J=6.1 Hz, 2H, OCH2), 3.80(s, 3H, OCH3), 2.78-2.67(m, 2H NCH2), 2.5 l(m, 4H NCH2), 1.49(m, 8H, CH2); Analysis calculated for C26H30N2O2: C, 77.58; H, 7.51; N, 6.96; found: C, 77.55; H, 7.53; N, 6.95.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; SANYAL, Sabyasachi; KUMAR, Atul; CHATTOPADHYAY, Naibedya; LAL, Jawahar; TRIVEDI, Arun Kumar; DATTA, Dipak; RATH, Srikanta Kumar; AKHTAR, Tahseen; DWIVEDI, Shailendra Kumar Dhar; YADAV, Manisha; CHAKRAVARTI, Bandana; SINGH, Abhishek Kumar; MISHRA, Jay Sharan; SINGH, Nidhi; TRIPATHI, Anil Kumar; WO2015/29068; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 26487-67-2

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Electric Literature of 26487-67-2,Some common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 1,1-bis(4-hydroxyphenyl)-2-phenylpent-1-ene (32.6 mg, 98.7 mumol) in DMF (0.99 mL) at 0 ¡ãC was added 60percent sodium hydride (dispersion in paraffin liquid, 31.6 mg, 0.790 mmol). The reaction mixture was stirred for 10 min at 50 ¡ãC and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (64.5 mg, 0.326 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 3.5 h at 50 ¡ãC, saturated aqueous ammonium chloride was added at 0 ¡ãC. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 9/1) to afford RID-F-S*12 (compound 11) (42.8 mg, 75percent) as a white solid

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.