CC BY-ND-NC 4.0 · SynOpen 2019; 03(04): 124-137
DOI: 10.1055/s-0039-1690334
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Room-Temperature, Base-Mediated Selective Synthesis of 2-(Arylamino)ethanols and 2-Aryloxyethanols

,
Swapnali R. Sonawane
,
Nishant K. Rasal
,
Department of Chemistry, Baburaoji Gholap College, Sangvi, Pune 411027, India (Affiliated to Savitribai Phule Pune University, Pune, India)   Email: sangeetajagtap@rediffmail.com
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Publication History

Received: 22 September 2019

Accepted after revision: 31 October 2019

Publication Date:
18 November 2019 (online)


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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®.

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