1-Benzyl-4-piperidone → 1-Benzyl-4-(3-bromo-2-ethylphenyl)piperidin-4-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-dibromo-2-ethyl-benzene (30 g, 113.65 mmol) in THF (150 mL) was added 45.5 mL of BuLi (2.5M in hexane, 113.65 mmol) under nitrogen. The mixture was stirred for 4 hr at −78° C. Then N-benzyl-4-piperidone (21.51 g, 113.65 mmol) was added to the above mixture and stirred overnight, The mixture was poured into sat. aqueous NH4Cl solution and extracted with DCM. The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure give the crude 1-benzyl-4-(3-bromo-2-ethyl-phenyl)-piperidin-4-ol (D116) (30.4 g). MS (ES): C20H24BrNO requires 373. found 374 (M+H+).

Provenance & Evidence