Benzyl Bromide → HCID 44553785, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzyl-2-(2-oxopiperidin-1-yl)isonicotinamide (0.14 g, 0.45 mmol) in anhydrous tetrahydrofuran (15 mL) was added a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (0.52 mL, 0.45 mmol) at −78° C. under nitrogen atmosphere. The resulting solution was stirred for 30 minutes at −78° C., followed by the addition of a solution of benzyl bromide (0.15 g, 0.90 mmol) in anhydrous tetrahydrofuran (5 mL) dropwise at −78° C. The reaction mixture was warmed to ambient temperature, stirred for 2 hours, quenched with aqueous saturated ammonium chloride solution (10 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 50-65% ethyl acetate in hexanes to give N-benzyl-2-(3-benzyl-2-oxopiperidin-1-yl)isonicotinamide as a colorless solid (0.06 g, 32%): 1H NMR (300 MHz, CD3OD) δ 8.61 (d, J=6.1 Hz, 1H), 7.98 (s, 1H), 7.58 (d, J=6.2 Hz, 1H), 7.42-7.12 (m, 10H), 4.58 (d, J=4.1 Hz, 2H), 2.88-2.81 (m, 2H), 2.1-1.91 (m, 4H), 1.81-1.58 (m, 3H); MS (ES+) m/z 400.5 (M+1).

Provenance & Evidence