Acetic Acid → 4-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}-1-cyclopropylmethylpiperidin-4-ol

Participants

Reaction Steps

A solution of 0.78 g (2.02 mmol) of 4-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenyl}piperidin-4-ol and 0.59 mL (8.06 mmol) of cyclopropanecarbaldehyde in 40 mL of THF was stirred for 30 minutes at RT, then combined with 1.71 g (8.06 mmol) of sodium triacetoxyborohydride and 0.46 mL (8.06 mmol) of glacial acetic acid and stirred for a further 2 days at RT. The reaction mixture was combined with DCM, and the organic phase was washed with semisaturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and evaporated down in vacuo. The crude product was stirred with isopropanol, and the precipitate was filtered off and dried in vacuo. Yield: 0.19 g (21% of theoretical); C28H27ClN2O (M=442.980); calc.: molpeak (M+H)+:443/445 (Cl); found: molpeak (M+H)+:443/445 (Cl); HPLC-MS: 7.26 minutes (method A).

Provenance & Evidence