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Synthesis 2004(2): 208-212
DOI: 10.1055/s-2003-44383
DOI: 10.1055/s-2003-44383
PAPER
© Georg Thieme Verlag Stuttgart · New York
Organic Reactions in Ionic liquids: N-Alkylation of Phthalimide and Several Nitrogen Heterocycles
Further Information
Received
28 July 2003
Publication Date:
15 December 2003 (online)
Publication History
Publication Date:
15 December 2003 (online)
Abstract
N-Alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in ionic liquids ([bmim]BF4 = 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim]PF6 = 1-butyl-3-methylimida-zolium hexafluorophosphate, [buPy]BF4 = butylpyridinium tetrafluoroborate) in the presence of potassium hydroxide as a base. In this manner, phthalimide, indole, benzimidazole, succinimide can be successfully alkylated. The procedure is convenient, efficient, and generally affords the N-alkylated product exclusively.
Key words
ionic liquids - N-alkylation - phthalimide - heterocycle
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