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

The Journal of organic chemistry (2007-12-07)
Feng Xu, Bryon Simmons, Robert A Reamer, Edward Corley, Jerry Murry, David Tschaen
RÉSUMÉ

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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Thionyl chloride, ReagentPlus®, ≥99%
Sigma-Aldrich
Thionyl chloride, reagent grade, 97%
Sigma-Aldrich
Thionyl chloride, ReagentPlus®, 99.5%, low iron