1-Benzyl-4-piperidone → 1,4-dibenzylpiperidin-4-ol

Participants

Reaction Steps

To a solution of benzyl magnesium chloride (40 ml of 2.0 M soln. in THF, 80 mmol)in THF (80 ml) was added 1-benzyl-4-piperidinone (7.4 ml, 40 mmol) over 7 min. and stirred overnight. The o reaction mixture was poured over ice and extracted with ether (2×). The combined ether extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo to a pale green syrup. This material was chromatographed on silica with 50-60% EtOAc/hexane as eluent. The appropriate fractions were combined and concentrated in vacuo to afford the product as an off white solid.

Provenance & Evidence