The chemistry of N-substituted benzotriazoles. Part 14. Novel routes to secondary and tertiary amines and to N, N-disubstituted hydroxylamines

Abstract

Tertiary amines of types R⁴R³CHNR¹R²(2), (R²CH₂)₂NR¹(10) and (11), or (R²CH₂)₃N (12), secondary amines of type (R²CH₂)₂NH (8), and N, N-disubstituted hydroxylamines of type (R²CH₂)₂NOH (9), are prepared in high yield by the action of Grignard reagents or sodium borohydride on easily available N, N-dialkyl-N-[benzotriazolylalkyl-(or arylalkyl-)]amines (1) or tris(benzotriazolylmethyl)amine (7), on bis(benzotriazolylmethyl)amines (3), (5), and (6), and on N, N-bis(benzotriazolylmethyl)hydroxylamine (4), respectively.