GB604363A - Manufacture of monoaryl tertiary amines or salts thereof - Google Patents

Abstract

Tertiary arylamines are obtained by treating a mono-salt of a compound of the formula A-NH-R-Y wherein R represents an alkylene chain, A represents an aryl radical and Y a more strongly basic group than A-NH, with a reactive ester of an alcohol. Mono-salts are derived from the following acids: hydrohalic acids, sulphuric acid, nitric and alkyl-, aralkyl-, or aryl-sulphonic acids. The alkylene chain may be branched or unbranched or also form part of a ring, specified residues being ethylene, propylene, decamethylene, 2 : 2-dimethyl-propylene and cyclohexylene. Y may represent a primary, secondary, or tertiary amino group, e.g. mono- or dialkyl amino, piperidino, napholino, guanidino, amidino, imidazolino, or tetrahydropyrimidino. Specified esters are derived from hydrohalic, alkyl-sulphonic and arylsulphonic acid; and aliphatic, araliphatic, alicyclic and heterocyclic alcohols. The reaction may be effected in the presence of a diluent, e.g. alcohol or dioxane, and of a catalyst such as sodium iodide, copper powder or copper chloride. In examples: (1) N-allyl-N-(b -dimethylamino-ethyl)-aniline is obtained by boiling N - (b - dimethylamino - ethyl) - aniline monohydrochloride with allyl bromide in absolute alcohol; (2) N-benzyl-N-(g -diethylamion-propyl)- is obtained by boiling N-(g -diethylamino - propyl) - aniline monohydrochloride (obtained from aniline and g -diethylamino - propyl chloride hydrochloride) with benzyl chloride in absolute alcohol (benzyl bromide or p-toluene sulphonic acid ester may be used instead of the chloride); (3) N-benzyl-N - (g - dimethylamino - propyl) - 2 - anisidine, is obtained by treating N(g -dimethylaminopropyl)-2-anisidine with benzyl chloride in alcohol solution; (4) N-benzyl-N-(b -methylamino-ethyl)-aniline, is obtained by reacting N - (b - methyl - amino - ethyl) - aniline monohydrochloride with benzyl chloride as above; (5) N - (b - amino - ethyl) - aniline is obtained by reacting N-(b -amino-ethyl)-aniline monohydrochloride with benzyl chloride; (6) 2-(N-phenyl-N-benzyl - amino - methyl) - imidazoline monohydrochloride, by reacting 2-(phenylaminomethyl)-imidazoline monohydrochloride with benzyl chloride in alcohol. Butyl alcohol, dioxane or in benzyl chloride itself may be used as the solvent. Other products which may be prepared by the process of the invention are listed. Samples have been furnished under Sect. 2 (5) of : (1) 2-[N-(31-oxyphenyl)-N-benzylaminomethyl]-imidazoline hydrochloride; (2) 2 - [N - (41 - chlorophenyl) - N - benzyl - aminomethyl] imidazoline hydrochloride; (3) N-phenyl - N - benzyl - amino - acetamidine - monohydrochloride; (4) 2 - (N - phenyl - N - benzyl - aminomethyl) - tetrahydropyrimidine, all prepared by the process of the invention as set out above. N - (g - dimethylaminopropyl) - 2 - anisidine is prepared by reacting g -dimethylaminopropyl chloride with 2-anisidine.