Diallylamine → HCID 90112871, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-1-(3-pyridyl)ethanone hydrobromide (10 g, 23.49 mmol) is added portion wise over 5 minutes to a stirred solution of diallylamine (5.2 mL, 42.29 mmol) and diisopropylethylamine (10.24 mL, 58.73 mmol) in tetrahydrofuran (150 mL) at 0° C. The resulting mixture is stirred at 0° C. for 1 hour. The reaction is quenched by addition of a saturated aqueous solution of sodium bicarbonate (100 mL) and dichloromethane (300 mL). The layers are separated and the aqueous phase is re-extracted with dichloromethane (300 mL). The combined organic layers are dried over magnesium sulfate and the solvents are removed under reduced pressure to give a crude product which is purified by silica gel column chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (4.75 g, 93%). ES/MS (m/e): 217 (M+1).

Provenance & Evidence