GB834313A - Improvements in and relating to the manufacture of diquaternary compounds - Google Patents

Abstract

Quaternary compounds of the formula <FORM:0834313/IV (b)/1> wherein R1 and R2 are each a cycloalkyl e.g. cyclohexyl group or a phenyl group optionally bearing halogen, C1-5 alkyl or C1-5 alkoxy substituents, X is -(CH2)n- or -(CH2)2.O. (CH2)2-, n being an integer from 2 to 10 and m is 2, 3 or an integer from 6 to 10, N1 + is a quaternary nitrogen atom carrying two alkyl groups, together having up to 5 carbon atoms, or forming part of a pyrrolidine, piperidine or morpholine ring, N2+ is a quaternary nitrogen atom carrying at least one alkyl group of 1 to 4 carbon atoms and either two further alkyl groups totalling up to 9 carbon atoms or forming part of a pyrrolidine, piperidine or morpholine ring and A- is an equivalent of an organic or inorganic anion e.g. halide or alkyl sulphate, are made by treating a mono-quaternary amine of the formula NC.C.(R1)(R2).X.\sNN1.(CH2)m.N3\h wherein N3 is a tertiary nitrogen atom, with a lower alkyl quaternizing agent such as an alkyl halide. In examples: (1) N-(5-cyano-5 : 5-diphenylpentyl) - N : N - dimethyl - N - (2-morpholinoethyl)-ammonium iodide is treated with methyl iodide to give the bis-quaternary salt; and (2) N-(5-cyano-5 : 5-diphenylpentyl)-N-(2-morpholinoethyl) pyrrolidinium iodide is treated with methyl iodide to give the bisquaternary salt. Many other products are specified. Mono-quaternary compounds of the formula II used as starting materials such as the starting materials of Examples (1) and (2) are made by the reaction of an amine of the formula NC.C(R1)(R2).X.N4 with a halide Z-(CH2)m-N3, wherein Z is a halogen atom.