GB604675A - Improvements in or relating substituted diamines - Google Patents

Abstract

Substituted diamines, therapeutically useful as anti-histaminic agents and of the general formula <FORM:0604675/IV(b)/1> (wherein R represents an alkyl group having at least two carbon atoms, or an aralkyl group, n is an integer greater than one, and the benzene nucleus may be substituted by alkyl groups), are manufactured by (a) condensing (if required in the presence of a condensing agent such as phosphorus pentoxide or zinc chloride) alkyl or aralkyl anilines (which may carry nuclear alkyl substituents and in which the group attached to the nitrogen atom contains at least two carbon atoms) with a compound of the type <FORM:0604675/IV(b)/2> (wherein X represents a halogen atom), or (b) condensing a substituted diamine of the type <FORM:0604675/IV(b)/3> (wherein the benzene nucleus may be substituted by alkyl groups) with an alkyl or aralkyl halide. Examples describe the condensation of N-ethyl-aand N-butyl-aniline with b -dimethylamino-a -chloroethane and of N-ethylaniline with g -dimethylamino-a -chloropropane. Specifications 274,058, [Class 2 (iii)], and 433,625 are referred to. A sample has been furnished under Sect. 2 (5) of the hydrochloride of N-phenyl-N-benzylN1:N1-dimethylethylenediamine, prepared by heating N - dimethylaminoethylaniline with benzyl chloride in aqueous sodium carbonate solution. The Specification as open to inspection under Sect. 91 comprises also the manufacture of similar products in which the methylene groups in the side chain may carry alkyl substituents, the group R may be unsaturated, and the benzene ring may carry substituents other than alkyl groups, e.g. alkoxy groups; and the use of other known methods of manufacture, e.g. the action of dimethylamine on N-(monohalogenoalkylene)-N-alkyl- (or aralkyl)-anilines in which the alkylene group contains more than one methylene or substituted methylene group and the alkyl (or aralkyl) group contains at least two carbon atoms. In additional examples, (a) N-butyl-p-toluidine (or N-butyl-p-anisidine or N-p-ethylbenzylaniline) and (b) N-allylaniline are condensed with b -dimethylamino-chlorethane. This subject-matter does not appear in the Specification as accepted.