Sodium hydride → 1-(Cyclopropylmethyl)-6-phenylazepan-2-one

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Reaction Steps

Sodium hydride (60% dispersion in mineral oil; 0.793 g, 19.8 mmol) was added to a solution of 6-phenylazepan-2-one (2.50 g, 13.2 mmol) and cyclopropylmethyl bromide (1.92 mL, 19.8 mmol) in N,N-dimethylformamide (30 mL) at 0° C., then the mixture allowed to warm to ambient temperature. After 18 h the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water (3×) and saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (1% methanol/dichloromethane→5% methanol/dichloromethane) gave the title compound (2.33 g). MS 244 (M+1).

Provenance & Evidence