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A facile synthesis of piperazines from primary amines
Author(s) -
Henry David W.
Publication year - 1966
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570030423
Subject(s) - chemistry , acetic anhydride , iminodiacetic acid , amine gas treating , primary (astronomy) , organic chemistry , borane , acetic acid , catalysis , physics , chelation , astronomy
A general procedure is described for converting primary amines to N ‐substituted piperazines. Reaction of an amine with an N ‐substituted iminodiacetic acid anhydride (V) yields an iminodiacetic acid monoamide (VI) which closes to a 2,6‐piperazinedione (VII) upon treatment with acetic anhydride. The diones are reduced to piperazines with borane‐THF. Fourteen examples of this process, using twelve aliphatic or aromatic amines and three iminodiacetic acids, are presented. Yields of piperazines, based upon starting amine, ranged from 21 to 52%. The procedure is rapid and no purification problems were encountered. Alternate methods for preparing the 2,6‐piperazinedione intermediates are discussed.