Tetrahedron

Reaction of 1, 2-dibromoethane with primary amines: formation of N, N′-disubstituted ethylenediamines RNH–CH 2 CH 2–NHR and homologous polyamines RNH–[ …

MK Denk, MJ Krause, DF Niyogi, NK Gill

Index: Denk, Michael K.; Krause, Mike J.; Niyogi, Debyani F.; Gill, Nachhattarpal K. Tetrahedron, 2003 , vol. 59, # 38 p. 7565 - 7570

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Citation Number: 15

Abstract

The reaction of primary amines RNH2 (R: Me, Et, iPr, tBu and Ph) with 1, 2-dibromoethane gave N, N′-disubstituted ethylenediamines R–NH–CH2CH2–NH–R (1) in yields ranging from 10%(1a; R= Me) to 70%(1d, R= tBu; 1e, R= Ph). Piperazines and N-substituted polyethyleneimines were identified (1H NMR, 13C NMR and EI-MS) as side products of the reaction and isolated by fractional distillation. The piperazines 2 are formed in yields of 3– ...