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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 13
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Original Articles

An Optimized Version of Gabriel-Type Nucleophilic Amination

Pages 2287-2293 | Accepted 30 Sep 1999, Published online: 04 Dec 2007
 

Abstract

N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(tbutoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-l. Deprotection of 2 by refluxing with ptoluenesulfonic acid in ethanol affords ammonium tosylates 3a-l in reasonable yields.

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