Triethylamine → 1-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine

Participants

Reaction Steps

A solution of triethylamine (0.987 mL, 7.08 mmol) in ethanol (6.2 mL) and methanol (4.2 mL) was treated with 1-(4-bromophenyl)piperidin-4-one (0.9 g, 3.54 mmol) and dimethylamine hydrochloride (0.578 g, 7.08 mmol). Titanium(IV) isopropoxide (2.075 mL, 7.08 mmol) was added and a thick mixture formed. The suspension was stirred at ambient temperature for 18 hours. Sodium borohydride (0.2 g, 5.31 mmol) was then added portion-wise over 5 minutes and the reaction mixture was stirred at ambient temperature for 18 hours. The reaction was quenched with 70 mL 10% aqueous ammonia and the resulting suspension was extracted with 250 mL dichloromethane. The aqueous layer was extracted with 150 mL additional dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was purified by flash chromatography on a silica gel column eluting with a gradient of from 0% to 7% methanol in dichloromethane to provide the title compound. MS ESI(+) m/z 284.8 [M+H]+.

Provenance & Evidence