Bourquin, J. P.’s team published research in Helvetica Chimica Acta in 41 | CAS: 4584-49-0

Bourquin, J. P. published the artcileSyntheses in the phenothiazine family. II. N-Substituted phenothiazinethiol derivatives, Formula: C5H13Cl2N, the publication is Helvetica Chimica Acta (1958), 1072-108, database is CAplus.

cf. C.A. 52, 18423d. 2-(N-Methyl-2-pyrrolidyl)ethanol (31.0 g.) in 200 ml. CHCl₃ treated with HCl 10 min. at 10°, 59.0 g. SOCl₂ added, after 2 hrs. at 70° the mixture concentrated, treated with 160 ml. 3N NaOH, extracted with Et₂O, and the dried extracts distilled gave 90% 2-(N-methyl-2-pyrrolidyl)-1-chloroethane (I), b₁₁ 65-6°; picrate, m. 133-5° (EtOH). BuNHMe (60.9 g.) and 54.6 g. Br(CH₂)₃Cl in boiling Et₂O 24 hrs. gave 68% BuMeN(CH₂)₃Cl, b₁₃ 71-2°; picrate, m. 94-6° (EtOH). BrCH₂CHMeCH₂Cl (68.6 g.), 36.0 g. Me₂NH, and 20 ml. C₆H₆ heated in an autoclave at 110° 7 hrs., 100 ml. H₂O and 320 ml. 10% HCl added, and the mixture extracted with 250 ml. Et₂O and 140 ml. 30% NaOH gave 68% Me₂NCH₂CHMeCH₂Cl, b₁₁ 35-6°. To 50.0 g. N-methylpiperazine in 150 ml. MeOH was added 37.7 g. propylene oxide, the mixture boiled 3 hrs., and distilled giving 70% N-methyl-N’-(2-hydroxypropyl)piperazine (II), b₁₁ 91-3°. II (50.7 g.) in 250 ml. C₆H₆ saturated with HCl, 78.2 g. SOCl₂ added, the mixture refluxed 5 hrs. then concentrated, 100 ml. H₂O and 120 ml. 30% NaOH added, the mixture extracted with 600 ml. C₆H₆, and the extract distilled gave 60% N-methyl-N’-(2-chloropropyl)piperazine, b₁₁ 87-9°; di-HCl salt, m. 233-5° (EtOH). N-Methylpiperazine (46.8 g.) and 40 g. BrCH₂CHMeCH₂Cl in 120 ml. refluxing Et₂O 24 hrs. gave 30% N-methyl-N’-(3-chloro-2-methylpropyl)piperazine, b₁₁ 99-100°; di-HCl salt, m. 234-6° (MeOH). Similarly, 233 g. N-benzylpiperazine and 104 g. Br(CH₂)₃Cl in 370 ml. Et₂O 48 hrs. gave 75% N-benzyl-N’-(3-chloropropyl)piperazine, b_0.01 132-6°; di-HCl salt, m. 249-51° (absolute EtOH). 2-(Methylthio)phenothiazine (III) (16.65 g.), 3.18 g. NaNH₂, and 100 ml. absolute xylene refluxed 3 hrs., 10.0 g. I in 10 ml. absolute xylene added during 1.5 hrs., after refluxing 3 hrs. and cooling 5 g. NH₄Cl and 150 ml. H₂O added, the xylene layer extracted with 115 ml. 15% tartaric acid, 35 ml. concentrated NaOH added, and the freed base extracted with 100 ml. C₆H₆ gave 85% 10-[2-(N-methyl-2-pyrrolidyl)ethyl]-2-(methylthio)phenothiazine, b_0.008 209°; tartrate, sintered 70°, m. 115°. Similarly prepared were the following 10-[2-(N-methyl-2-pyrrolidyl)ethyl]-2-(alkylthio)phenothiazines (alkyl groups given): Et, b_0.01 213° (tartrate-0.5-H₂O, sintered 65°, m. 90°); iso-Pr, b_0.008 217° (tartrate-0.5H₂O, sintered 70°, m. 90°); Bu, b_0.01 225° (tartrate-0.5H₂O, sintered 60°, m. 75°). 10-[2-(N-Methyl-2-piperidyl)ethyl]-2-(alkylthio)phenothiazines (alkyl groups given): Et (IV) [80% from 18.89 g. 2-(ethylthio)phenothiazine (V) and 14.7 g. 2-(N-methyl-2-piperidyl)-1-chloroethane], b_0.008, m. 57-9° (iso-PrOH) (tartrate, sintered 70°, decompose 135°); Pr, b_0.01 247° (tartrate, sintered 70°, decompose 120°); iso-Pr, b_0.05 223°, m. 73-5° (tartrate, sintered 70°, decompose 120°); Bu, b_0.005 227°; iso-Bu, b_0.003 215°; sec-Bu, b_0.007 215°; n-hexyl, b_0.015 235°; PhCH₂ (VI), b_0.01 246° (tartrate-0.5-H₂O, sintered 75°, m. 105°). 10-(N-Methyl-3-piperidylmethyl)-2-alkylphenothiazines (alkyl groups given): Me [60% from 50.0 g. III and 33.8 g. N-methyl-3-(chloromethyl)piperidine], b_0.01 207° [HCl salt, sintered 110°, decompose 124-6° (Me₂CO); tartrate-0.5H₂O, sintered 75°, decompose 140° (EtOAc); oxalate, decompose 182-4° (absolute EtOH)]; Et, b_0.01 222° (tartrate, sintered 75°, m. 140°); Pr, b_0.01 225°, sintered 85°, m. 145°; iso-Pr, b_0.01 216° (tartrate-0.5H₂O, sintered 75°, decompose 140°); Bu, b_0.01 223° (tartrate, sintered 80°, decompose 100°); iso-Bu, b_0.005 207° (tartrate-0.5H₂O, sintered 85°, m. 120°); sec-Bu, b_0.005 206°, tartrate-0.5H₂O, sintered 80°, m. 110°); PhCH₂, b_0.007 236° (tartrate-H₂O, sintered 90°, m. 120°). 10-(3-Dimethylaminopropyl)-2-(alkylthio)phenothiazines (alkyl group given): Et (80-5% from 20.0 g. V and 11.3 g. Me₂N(CH₂)₃Cl), b_0.008 200° [tartrate, sintered 110°, m. 117-9° (absolute EtOH)]; Pr, b_0.02 227° (tartrate-0.5H₂O, sintered 55°, decompose 90°); iso-Pr, b_0.01 198° (tartrate-0.5H₂O, sintered 60°, decompose 90°; oxalate, decompose 206-8°); Bu, b_0.005 202°; iso-Bu, b_0.004 195°; sec-Bu, b_0.006 189°; PhCH₂, b_0.01 224° (tartrate, sintered 65°, m. 85°). 10-Dialkylaminoalkyl-2-(methylthio)phenothiazines (dialkylaminoalkyl groups given): Me₂NCH₂CH₂ (85% from 50.0 g. III and 22.0 g. Me₂NCH₂CH₂Cl), b_0.01 195-6°, m. 72-4° (iso-PrOH) [HCl salt, m. 175-7° (absolute EtOH)]; Et₂NCH₂CH₂, b_0.01 198° (HCl salt, m. 160-2°); Et₂NCHMeCH₂, b_0.01 182° (HCl salt, sintered 194°, m. 202-4°); 2-(N-pyrrolidyl)ethyl, b_0.01 219-21°, m. 73-5° (HCl salt, m. 170-2°); 2-(N-methyl-N’-piperazyl)ethyl, b_0.02 228-30°, m. 85-7° (di-HCl salt, decompose 243-5°); 3-(N-piperidyl)propyl, b_0.05 235-7° (tartrate, sintered 65°, decompose 100°; methobromide, sintered 165°, m. 178-80°); 3-(N-benzyl-N’-piperazyl)propyl, m. 82-4° (di-HCl salt, sintered 225°, decompose 236-8°); 3-(N-morpholyl)propyl, b_0.03 240-2°, m. 100-2° (HCl salt, sintered 146°, m. 152-4°); 2-(N-pyrrolidyl)propyl, b_0.015 204° (HCl salt, m. 177-9°); 2-(N-methyl-N’-piperazyl)propyl, b_0.01 211° (di-HCl salt-0.5H₂O, sintered 210°, m. 224-6°). 10-Dialkylaminoalkyl-2-(isopropylthio)phenothiazines: Me₂NCH₂CH₂, b_0.015 189° (HCl salt, m. 182-4°); Et₂NCH₂CH₂, b_0.01 187° (HCl salt, m. 162-4°);

Helvetica Chimica Acta 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, Formula: C5H13Cl2N.

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