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CC BY-ND-NC 4.0 · SynOpen 2019; 03(04): 124-137
DOI: 10.1055/s-0039-1690334
DOI: 10.1055/s-0039-1690334
paper
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
› Author Affiliations
Further Information
Publication History
Received: 22 September 2019
Accepted after revision: 31 October 2019
Publication Date:
18 November 2019 (online)
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 controlledSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690334.
- Supporting Information
-
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For ticlopidine synthesis:
For vildagliptin synthesis:
For gemfibrozil synthesis: