RUTHENIUM CATALYZED N-ALKYLATION OF AMIDES WITH ALCOHOLS.

Article abstract of DOI:10.1246/bcsj.56.2647

Amides reacted with primary alcohols in the presence of a catalytic amount of RuCl//2(PPh//3)//3 at 180 degree C to give the corresponding N-monoalkyl amides in fairly good yields. Thus, benzamide reacted with l-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 amides. But formamide reacted with l-butanol to give N,N-dibutylformamide, as well as N-butylformamide, in low yield. RuCl//2(PPh//3)//3 was the most effective catalyst for this reaction and RuHCl(PPh//3)//3 also had some catalytic activity.