Phosgene → HCID 9868930, compound

Participants

Reaction Conditions

Reaction Steps

4-[2-(Morpholin-4-yl)ethoxy]napth-1-yl-amine (280 mg, 1.0 mmol) was dissolved in dichloromethane (15 mL). An equal volume of sat. aqueous sodium bicarbonate was added, and the biphasic solution was cooled to 0° C. During the addition of phosgene (1.93 M in toluene, 1.0 mL), stirring was stopped. Immediately afterward, stirring was resumed for 15 min with the reaction mixture at 0° C. The layers were separated, the organics were dried over solid magnesium sulfate and concentrated to approximately 5 mL of solution. 5-tert-Butyl-2-methylaniline (150 mg, 0.9 mmol) in dichloromethane (5 mL) was added, and the reaction mixture was stirred for 17 h at ambient temperature. The desired compound was obtained after treatment of the reaction mixture with petroleum ether and filtering to collect the precipitate (180 mg, 42%).

Provenance & Evidence