Studies on the Reactions of Aliphatic Amines with Epoxypropane-derivatives and their Products. II

Abstract

By the reaction of several aliphatic secondary amines with epichlorohydrin, N-(γ-chloro-β-hydroxypropyl) amino compounds were isolated. These compounds were turned easily into quarternary ammoium compounds by standing for long period of time or by heating of their aqueous solution, but it was found that a complete quarternarisation was difficult in case of N, N'-bis(γ-chloro-β-hydroxypropyl) pipe-razine. However, N-(γ-chloro-β-hydroxypropyl) amino compounds or quarternary ammonium compounds were unable to be isolated from the reaction product of aliphatic primary amines with epichlorohydrin. Reactions of aliphatic amines and glycidolsulfonic acid esters gave products difficult for isolation of N-(γ-sulfonyloxy-β-hydroxypropyl) amino compounds but resulted in a directive formation of quarternary ammonium compounds, except for the reaction of piperazine and glycidol-p-toluenesulfonic acid esters. It was confirmed that these quarternary ammonium compounds were formed only as an intramolecular reaction resulting in the azetidinium ring.