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Spontaneous conversion of O-tosylates of 2-(piperazin-1-yl)ethanols into chlorides during classical tosylation procedure.

ABSTRACT: A direct conversion of piperazinyl ethanols into chlorides via a classical O-tosylation protocol is observed. The acceleration of the transformation by the piperazine unit is demonstrated. It is found that the reaction goes via the corresponding O-tosylate, which converts spontaneously into chloride with different rate depending on the substrate structure. In the case of pirlindole derivative, partially aromatized chloride formation was observed upon prolongation and/or increased excess of tosyl chloride.

SUBMITTER: Kurteva VB 

PROVIDER: S-EPMC6408397 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Spontaneous conversion of <i>O</i>-tosylates of 2-(piperazin-1-yl)ethanols into chlorides during classical tosylation procedure.

Kurteva Vanya B VB   Shivachev Boris L BL   Nikolova Rositsa P RP  

Royal Society open science 20190213 2

A direct conversion of piperazinyl ethanols into chlorides via a classical <i>O</i>-tosylation protocol is observed. The acceleration of the transformation by the piperazine unit is demonstrated. It is found that the reaction goes via the corresponding <i>O</i>-tosylate, which converts spontaneously into chloride with different rate depending on the substrate structure. In the case of pirlindole derivative, partially aromatized chloride formation was observed upon prolongation and/or increased e  ...[more]

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