Chlorination/cyclodehydration of amino alcohols with SOCl2: an old reaction revisited.

J Org Chem

Department of Process Research, Merck Research Laboratory, Rahway, New Jersey 07065, USA.

Published: January 2008

AI Article Synopsis

  • The study introduces a straightforward method for creating cyclic amines through chlorinating amino alcohols using thionyl chloride (SOCl2).
  • This new technique simplifies the process by eliminating the traditional multi-step sequence, which typically involves protecting and activating groups before cyclization and then removing them.
  • The research also explores the various reaction pathways and the broader applicability of this method in transforming amino alcohols into cyclic amines.

Article Abstract

A simple, one-pot preparation of cyclic amines via efficient chlorination of amino alcohols with use of SOCl(2) has been developed. This approach obviates the need for the classical N-protection/O-activation/cyclization/deprotection sequence commonly employed for this type of transformation. The reaction pathways and the general scope of this method have also been investigated.

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http://dx.doi.org/10.1021/jo701877hDOI Listing

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