Water → 4-(3,5-Dimethylphenyl)-1-(phenylmethyl)-4-piperidinol

Participants

Reaction Conditions

Reaction Steps

5 mL (36.8 mmol) of 5-bromo-m-xylene were dissolved in 40 mL of dry THF under a nitrogen atmosphere. The resulting solution was cooled to −50° C. and 36.5 mL (58.4 mmol) of a 1.6 M solution of n-BuLi in hexane were added dropwise. The reaction mixture was stirred 30 min, then a solution of 10.3 mL (58.4 mmol) of 1-benzyl-4-piperidone in 20 mL of dry THF was added dropwise; stirring was continued for 1 h at −50° C., then the reaction mixture was allowed to warm to room temperature overnight. Water was added carefully and TIF was removed in vacuo; the resulting aqueous solution was extracted with AcOEt, the organic phase was dried and the solvent was removed in vacuo. The resulting crude product was purified by flash chromatography, eluting with a mixture CH2Cl2/MeOH/conc. NH4OH 100:2:0.4 respectively, yielding 5.44 g of the title compound.

Provenance & Evidence