Sodium hydride → 1-([1,1'-Biphenyl]-3-ylmethyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one

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Reaction Conditions

Reaction Steps

A solution of 6-(2,6-dimethoxyphenyl)piperidin-2-one (70 mg; 0.29 mmol; 1.0 equiv.) in anh. DMF (3 ml) was treated at rt with NaH (60% dispersion in mineral oil; 71 mg; 1.78 mmol; 6.0 equiv.), and 3-(bromomethyl)-1,1′-biphenyl (110 mg; 0.44 mmol; 1.5 equiv.). The resulting mixture was then heated to 60° C., under nitrogen, for 1 h. The reaction mixture was allowed to cool to rt, and a solution of aq. sat. NaHCO3 (10 ml) was added. After extractions with AcOEt (2×20 ml), the mixed organic layers were further washed with brine (10 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by preparative HPLC afforded 1-([1,1′-biphenyl]-3-ylmethyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one as a colorless oil. LC-MS (conditions A): tR=0.95 min.; [M+H]+: 402.16 g/mol.

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