Bulletin of the Chemical Society of Japan

The ruthenium catalyzed N-alkylation of amides with alcohols

Y Watanabe, T Ohta, Y Tsuji

Index: Watanabe; Ohta; Tsuji Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 9 p. 2647 - 2651

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Citation Number: 45

Abstract

Amides reacted with primary alcohols in the presence of a catalytic amount of RuCl 2 (PPh 3) 3 at 180° C to give the corresponding N-monoalkyl amides in fairly good yields. Thus, benzamide reacted with 1-octanol to give N-octylbenzamide in 76% yield with excellent product selectivity. Little esterification of amides with alcohols occurred and selectivity to the N-alkylation was high. Most of the amides gave N-monoalkyl amides but no N, N-dialkyl ...