1-Chloroethyl chloroformate → HCID 14850201, compound

Participants

Reaction Steps

A solution of 1-chloroethyl chloroformate (9.7 ml, 90 mmol) in 1,2-dichloroethane (25 ml) was added to an ice-chilled solution of N-(2-pyrazinyl)-N-(1-phenylmethyl-4-piperidinyl)-2-furanamide (45 mmol) and 1,2-dichloroethane (125 ml). The reaction mixture was stirred under reflux for 5 hours, then cooled and concentrated under vacuum. The crude carbamate residue was dissolved in methanol (150 ml) and the reaction solution was heated under reflux for 2 hours. The reaction solution was cooled, decolorizing carbon (10 g, Darco G-60) was added to the mixture, then the suspension was heated and stirred under reflux for 15 minutes. The suspension was filtered through Celite and the filtrate was concentrated under vacuum. The residue was suspended in hot isopropanol (100 ml), then cooled and filtered. The pale maize colored powder was dried under vacuum (85° C., 0.01 mm Hg, 2 hours) to yield N-(2-pyrazinyl)-N-(4-piperidinyl)-2-furanamide (8.9 g, 72%) as the hydrochloride salt.

Provenance & Evidence