Isobutyryl chloride → HCID 18538606, compound

Participants

Reaction Steps

To a stirred solution of 4-benzyl-1-(trifluoroacetyl)piperidine (4.34 g, 16.0 mmol) and isobutyryl chloride (2.18 mL, 20.8 mmol) in dichloromethane (50 mL) was added aluminum chloride (5.33 g, 40.0 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water (50 g), the organic layer was separated and the aqueous layer was extracted with dichloromethane (30 mL) The combined organic layers were washed with saturated aqueous sodium bicarbonate solution (3×15 mL), brine (15 mL), dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using ethyl acetate/hexane (1/19 to 1/9) as eluent to afford the title compound (3.60 g, 10.5 mmol, 66%) as a colorless oil.

Provenance & Evidence