Triethylamine → HCID 15462960, compound

Participants

Reaction Steps

In 50 ml of dichloromethane, 8.0 g (28.9 mmol) of 1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4-hydroxypiperidine were dissolved, followed by the addition of 2.92 g (28.9 mmol) of triethylamine. To the resulting mixture, a solution of 3.31 g (28.9 mmol) of methanesulfonyl chloride in 10 ml of dichloromethane was added dropwise under ice cooling, followed by stirring at room temperature for 1 hour. The solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and triethylamine hydrochloride so precipitated was filtered off. The filtrate was concentrated by evaporation under reduced pressure, whereby crude 1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4-methylsulfonyloxypiperidine was obtained. To the crude product, 50 ml of dimethylsulfoxide (DMSO) and 19.8 g (170 mmol) of potassium thioacetate were added and the resulting mixture was stirred at 50° C. for 4 hours. After the addition of water, the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethylacetate=19/1), whereby a reddish brown oil was obtained. The resulting oil was crystallized from hexane, whereby 3.6 g of the title compound were obtained as light brown crystals (yield: 37%).

Provenance & Evidence