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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.

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