Sodium hydride → 1-(4-(Benzyloxy)benzyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one

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Reaction Conditions

Reaction Steps

A mixture of 6-(2,6-dimethoxyphenyl)piperidin-2-one (110 mg; 0.46 mmol) in anh. DMF (2 ml) was treated at rt with NaH (60% dispersion in mineral oil; 118 mg; 2.95 mmol), and with commercially available 1-(benzyloxy)-4-(chloromethyl)benzene (130 mg; 0.56 mmol). The resulting mixture was then heated to 60° C., under nitrogen, for 1 h. After cooling to rt, aq. sat. NaHCO3 was added, and this mixture was extracted with AcOEt (2×). The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (AcOEt) afforded 1-(4-(benzyloxy)benzyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one as a yellow oil. LC-MS (conditions E): tR=0.82 min.; [M+H]+: 432.24 g/mol.

Provenance & Evidence