GB584584A - Improvements relating to the manufacture of benzylamine derivatives - Google Patents

Abstract

p-Acylaminomethyl phenyl alkyl sulphones are obtained by treating an alkali metal or alkaline earth metal salt of a p-acylamino methyl benzene sulphinic acid with an alkylating agent. Specified alkylating agents are methyl iodide, propyl p bromide, hexyl bromide and hexadecyl iodide. The sulphone thus produced may then be de-acylated by hydrolysis to yield the corresponding p-aminomethyl phenyl alkyl sulphone. In examples: (1) sodium p-acetamidomethyl phenyl alkyl sulsodium p-acetamidomethyl benzene sulphinate, suspended in aqueous alcohol, is heated under reflux with methyl iodide, and the reaction-mixture is evaporated in vacuo to isolate p - acetamidomethylphenyl methyl sulphone, which is hydrolysed by heating under reflux with (a) 3-N-hydrochloric acid, or (b) 3-N-sodium hydroxide to obtain p-aminomethyl phenyl methyl sulphone hydrochloride or the free sulphone, which is converted into the hydrochloride; (2) sodium p-acetamidomethyl benzene sulphinate is treated, as in (1), with n-propyl bromide, the product being heated under reflux with 3-N-hydrochloric acid to isolate p-aminomethyl phenyl n-propyl sulphone hydrochloride. Analogously, by using n-butyl-, or n-hexyl bromide, n-hexadecyl iodide, benzyl chloride, or ethylene dibromide, p-aminomethyl-phenyl n-butyl-, p-aminomethylphenyl n-hexyl-, p-aminoethylphenyl n-hexadecyl- and p-amino-methylphenyl benzyl-sulphone hydrochlorides, or a : b -bis-(p-aminomethylphenyl sulphonyl)-ethane dihydrochloride, may be obtained; (3) sodium p-acetamidomethyl benzene sulphinate, in water, is treated with dimethyl sulphate and sodium bicarbonate, and the solution is evaporated in vacuo to isolate p-acetamidomethylphenyl methyl sulphone which is hydrolysed by 3-N-hydrochloric acid to p-aminomethylphenyl methyl sulphone hydrochloride. p-Acetamidomethylbenzene sulphinic acid is prepared by treating p-acetamidomethylbenzene sulphonyl chloride with aqueous sodium sulphite and sodium bicarbonate, when sodium p-acetamidomethylbenzene sulphinate is deposited, from which the free acid is isolated by carefully acidifying the cooled aqueous solution.