Piperidine → HCID 89580877, compound

Participants

Reaction Steps

To a solution of methyl 4-formyl-2-methylbenzoate (300 mg, 1.7 mmol) and piperidine (92 mg, 1.1 mmol) in methanol (50 mL) was added acetic acid (1 drop) followed by sodium cyanoborohydride (221 mg, 3.5 mmol). The mixture was stirred at room temperature for 24 hours. The mixture was filtered, acidified with concentrated hydrochloride acid (1 mL) and concentrated in vacuo. To the residue, water (50 mL) was added. The mixture was extracted with dichloromethane (50 mL). The combined organic phase was separated, dried by sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1, 1% NH3) to give methyl 2-methyl-4-(piperidin-1-ylmethyl)benzoate as a yellow oil (200 mg, 60%). LRMS (M+H+) m/z: calcd 247.16. found 247. 1H NMR (300 MHz, CDCl3): δ 7.73 (d, J=8.7 Hz, 1H), 7.52-7.50 (m, 2H), 3.91 (s, 3H), 3.62 (s, 2H), 2.52 (s, 3H), 2.32-2.24 (m, 4H), 1.47-1.44 (m, 6H).

Provenance & Evidence