On the Cleavage of Tertiary Amines with Ethyl Chloroformate

Abstract

Forty-seven tent. amines were examined in order to observe the relative lability of the various N-substituents in respect to cleavage by ClCO2Et in refluxing benzene. The aromatic amines did not react with ClCO2Et, while aliphatic and alicyclic amines were cleaved to give carbamate(s); the tendency to cause R-N cleavage was: benzyl>allyl> methyl>ethyl>other alkyl groups. It was found that the reaction of a tert, amine with ClC02Et is greatly influenced by the polarity of the solvent, reaction temperature and N-substituents. © 1976, The Pharmaceutical Society of Japan. All rights reserved.