GB601615A - Improvements in or relating to the production of arylaliphatic diamines - Google Patents

Abstract

Araliphatic diamines of the general formula <FORM:0601615/IV(b)/1> wherein the benzene ring may be further substituted or not, R represents an aryl or heterocyclic nucleus (other than or pyrimidine nucleus) which may be substituted, e.g. by an alkyl or alkoxy group or a halogen atom, R1 represents hydrogen or an alkyl group, and R2 represents an alkyl group, are manufactured by condensing compounds of the type R.X with compounds of the general formula <FORM:0601615/IV(b)/2> (one of the symbols X and Y representing the group - NHR1 and the other a halogen atom) The products may be used as starting materials for industrial products such as detergents or vulcanization accelerators, whilst many of them posses pharmaceutical properties of value in human or veterinary medicine. In examples: (1) 1 - diethylaminomethyl - 4 - bromomethyl - benzene hydrobromide is heated with excess of N-ethylaniline in alcohol to produce 1-diethylaminomethyl - 4 - (N - phenyl - N - ethyl) - amino - methylbenzene; (2) 6-methoxy-8-aminoquinoline similarly yields 6-methoxy-8-(41-diethylaminomethyl)-benzylaminoquinoline; (3) 1-dimethylaminomethyl - 4 - bromomethylbenzene is used in place of the corresponding diethylamino derivative in (2); (4) 1-diethylaminomethyl-2 : 5 - dimethyl - 4 - bromomethylbenzene is similarly employed; (5) 2-methoxy-6 : 9-dichloroacridine is heated with 1-diethylaminomethyl-4-aminomethylbenzene in phenol to give 2-methoxy-6-chloro-9-(41-diethylaminomethyl) -benzylaminoacridine. Specifications 363,392, 437,953, 441,007, 441,132, 581,334 and 592,928 are referred to. The Specification as open to inspection under Sect. 91 comprises also the manufacture of other diamines of the general formula <FORM:0601615/IV(b)/3> wherein Ar represents a substituted or unsubstituted aryl nucleus, R an aryl or heterocyclic nucleus and R1 hydrogen or an alkyl group, and R2 and R3 may be the same or different and may represent alkyl or aralkyl groups or together may form with the nitrogen atom to which they are attached a heterocyclic ring, which may contain a second hetero atom (e.g. oxygen or nitrogen). This subject-matter does not appear in the Specification as accepted.ALSO:Araliphatic diamines of the general formula <FORM:0601615/IV (c)/1> wherein the benzene ring may be further substituted or not, R represents an acridine nucleus which may be substituted, e.g. by an alkyl or alkoxy group or a halogen atom, R1 represents hydrogen or an alkyl group, and R2 represents an alkyl group, are manufactured by condensing compounds of the type R.X with compounds of the general formula <FORM:0601615/IV (c)/2> (one of the symbols X and Y representing the group -NHR1 and the other a halogen atom). The products may be used as starting material for industrial products such as detergents or vulcanization accelerators, whilst many of them possess pharmaceutical properties of value in human and veterinary medicine. In an example, 2 - methoxy - 6 : 9 - dichloroacridine is heated with 1 - diethylaminomethyl-4-aminomethylbenzene in phenol to give 2-methoxy-6-chloro - 9 - (41 - diethylaminomethyl) - benzyl - aminoacridine. Specifications 363,392, 437,953, 441,007, 441,132, 581,334 and 592,928 are referred to.