Ofner, P. published the artcileAmidone. Some isomeric chlorodialkylaminopropanes and their reaction with diphenylmethyl cyanide, Recommanded Product: 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, the publication is Journal of the Chemical Society (1951), 1800-3, database is CAplus.
MeCH(NMe2)CO2Et is reduced by the Bouveault-Blanc procedure to 55% of MeCH(NMe2)CH2OH (I), b. 145-8° (picrate, orange-yellow, m. 182-3°); 20 g. I in 45 cc. C6H6, added (20 min.) to 23 g. SOCl2 in 90 cc. C6H6 at 0°, allowed to warm to room temperature, and refluxed 1.5 h., give 59% MeCH(NMe2)CH2Cl.HCl (II), m. 103-4°. Me2NCH2CHMeOH (III) yields a picrate, orange-yellow, m. 83-4°. III (20 g.) and 23 g. SOCl2, as above, give 73% Me2NCH2CHMeCl.HCl (IV), m. 190-1°. I (20 g.) in 45 cc. C6H6, treated with 23 g. SOCl2 in 90 cc. C6H6 and the gummy residue refluxed with 150 cc. Me2CO, gives 34% IV; the II is removed by the Me2CO. 1-Piperidino-2-propanol (b762 198-201°; picrate, m. 134-5°) gives with SOCl2 2-chloro-1-(1-piperidyl)propane-HCl (V), m. 213-14°. 1-(1-Piperidyl)-3-propanol (m. 66-7°) with SOCl2 gives 1-chloro-3-(1-piperidyl)propane (VI), b10 79-80°; HCl salt, m. 213-14°. The mother liquor from V or VI did not contain the other isomer. 1-Allylpiperidine (picrate, m. 72-3°) does not add HCl. The base, Me2NCH2CHMeCl (VII), liberated from IV by dilute NH4OH at 0° or with 40% NaOH at room temperature, is stable and gives the same picrate, even after distillation (b35 36-7°). The base liberated from II at room temperature by 40% NaOH solution is Me2NCHMeCH2Cl (VIII) (Schultz, et al., C.A. 42, 4934i). VIII can be heated in an inert solvent and can be agitated in an inert solvent with NaOH or NaNH2 without undergoing decomposition or isomerization; on distillation in vacuo, VIII is isomerized and VII and VIII can be separated by fractional crystallization of the picrates. The relative proportions of the isomers formed in the alkylation of PhCH2CN with VII or V were determined by effecting as complete as possible a separation of the isomers giving the more sparingly soluble salts. In the dimethylamino series, the N-compounds from the more sparingly soluble salts, whereas in the analogous piperidyl series, the salts of the iso compounds have the lowest solubility In the former series at least 60% of the cyanide was formed by isolation as 6-dimethylamino-4,4-diphenyl-3-heptane-HBr and in the latter at least 45% of the isocyanide as 3-imino-5-methyl-4,4-diphenyl-6-(1-piperidyl)hexane-2HCl. Thus, the relative proportions vary according to the nature of the basic groups of the Cl base employed in the alkylation.
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 C5H13Cl2N, Recommanded Product: 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride.
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