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Reaction of 1,2-dibromoethane with primary amines: formation of N,N′-disubstituted ethylenediamines RNH–CH2CH2–NHR and homologous polyamines RNH–[CH2CH2NR]n–H

✍ Scribed by Michael K Denk; Mike J Krause; Debyani F Niyogi; Nachhattarpal K Gill

Book ID
104205692
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
131 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

The reaction of primary amines RNH 2 (R: Me, Et, iPr, tBu and Ph) with 1,2-dibromoethane gave N,N 0 -disubstituted ethylenediamines R-NH -CH 2 CH 2 -NH-R (1) in yields ranging from 10% (1a; R¼Me) to 70% (1d, R¼tBu; 1e, R¼Ph). Piperazines and N-substituted polyethyleneimines were identified ( 1 H NMR, 13 C NMR and EI-MS) as side products of the reaction and isolated by fractional distillation. The piperazines 2 are formed in yields of 3 -10% and can be separated from the diamines 1 in all cases, except for R¼Me and Ph. The polyamine homologues RNH-[CH 2 CH 2 NR] n -H (3-5) were isolated in yields ranging from 0.1% (n¼4, R¼iPr) to 14% (n¼2, R¼iPr). The yields of 1 increase with the size of the substituent R, no obvious trend exists for the yields of the side products.

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