Room-Temperature, Base-Mediated Selective Synthesis of 2-(Arylamino)ethanols and 2-Aryloxyethanols

Abstract

A simple and efficient protocol for base-mediated selective synthesis of 2-(arylamino)ethanols from primary aromatic amines and 2-aryloxyethanols from phenols, promoted by K₂CO₃ has been achieved under mild conditions. Even in presence of excess alkyl halide, selective mono-N-alkylation has been achieved. Tolerance of a variety of functional groups is demonstrated by 15 examples of selective N-alkylation of aromatic amines and 19 examples of O-alkylation of phenols. The efficacy of the protocol is demonstrated by the formal synthesis of Ticlopidine^­®, Vildagliptin^®, Quetiapine^®, and Gemfibrozil^®.

Key words

selective N-alkylation - 2-(arylamino)ethanols - amines - 2-aryloxyethanols - phenols - K₂CO₃ promoted - Na₂CO₃ controlled

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