Triethylamine → 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]-1-piperidine methanesulfonamide

Participants

Reaction Steps

A stirred solution of 4-[2-(2,3-dimethoxyphenyl)-1-hydroxyethyl]piperidine (10.0 g, 0.037 mol) and Et3N (5.7 ml) in CH2Cl2 (75 ml) was cooled to 5° C. and methanesulfonyl chloride (3.6 g, 0.03 mol) was added dropwise so that the temperature did not rise above 10° C. The reaction was allowed to stand at ambient temperature for 1 h, and the reaction was concentrated in vacuo. The residue was treated with water, resulting in the formation of a white solid, which was collected to afford 10 g of the sulfonamide. The solid was recrystallized from toluene to yield the titled compound, and an additional recrystallization of this, gave 0.8 g of the analytically pure product as a white solid, mp 112-114° C.

Provenance & Evidence