Abstract
AbstractHerein a practical and efficient potassium tert-butoxide (KO t Bu)-facilitated amination of carboxylic acids with N,N-dimethylamine is described. In the presence of catalytic amount of KO t Bu, a variety of aliphatic and aromatic carboxylic acids are transformed to N,N-dimethylamides using DMF as the dimethylamine reagent with the assistance of trimethylacetic anhydride. The applicability of this protocol is demonstrated by late-stage dimethylamidation of complex drug molecules. A plausible reaction mechanism involving KO t Bu-facilitated in situ amine generation from formamide decomposition and anhydride-mediated condensation is proposed on the basis of mechanistic investigations.
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