1-Benzyl-4-piperidone → 1-Benzyl-4-(4-methoxyphenyl)piperidin-4-ol

Participants

Reaction Conditions

Reaction Steps

(4-Methoxyphenyl)magnesium bromide (0.5 M in THF, 90 mL, 45.0 mmol) was added slowly (˜25 minutes) via cannula to a cold (0° C.) solution of 1-benzylpiperidin-4-one (5.4 mL, 30.2 mmol) in THF (60 mL). The reaction was stirred at 0° C. under nitrogen for 2 hours. The reaction was quenched with saturated aqueous NH4Cl then diluted with ether. The organic fraction was washed with saturated aqueous NH4Cl (2×) brine (1×) and concentrated. Purification using flash chromatography (5-100% EtOAc/hexane) provided 4.02 g (44%) of the titled compound. MS (DCI) m/z 298 (M+H)+.

Provenance & Evidence