Piperidine → 2-Methyl-2-(1-thiocarbamoylpiperidin-4-yl)propionic acid ethyl ester

Participants

Reaction Steps

To a solution of 9-fluorenylmethoxycarbonylisothiocyanate (2.62 g, 9.32 mmol) in chloroform (20 ml), a solution of 2-methyl-2-piperidin-4-yl-propionic acid ethyl ester hydrochloride (2.27 g, 9.61 mmol) in chloroform (10 ml) and sodium hydrogen carbonate (4.03 g, 48.0 mmol) were added and the mixture was stirred at room temperature. Further, piperidine (30 ml) was added and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated in vacuo, and the solid obtained by adding diethyl ether was collected by filtration. The solid was dissolved in N,N-dimethylformamide (20 ml) and piperidine (20 ml) was added and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and the solution was extracted with ethyl acetate. The organic layer was washed with a saturated brine and dried over sodium sulfate, and the residue obtained by vacuum concentration was purified by silica gel chromatography (n-hexane:ethyl acetate) and the title compound (2.4 g, 98%) was obtained.

Provenance & Evidence