Dimethylformamide → 4-[2-(4-Trifluoromethoxyphenoxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Sodium hydride (60% in oil, 2.12 g) wad added to an N,N-dimethylformamide solution (100 ml) of 4-trifluoromethoxyphenol (9.0 g) under ice cooling and stirred for 30 minutes. After adding 4-[2-(toluene-4-sulfonyloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester (17.7 g), the mixture was heated to room temperature and stirred. The mixture was further stirred at 50° C. for 1 hour. After cooling the reaction mixture to room temperature, water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The result was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=67:33) to afford the title compound as a pale yellow oil (18.64 g).

Provenance & Evidence