Dimethylcarbamoyl Chloride → HCID 70579501, compound

Participants

Reaction Steps

Add in small portions with stirring, 360 mg of sodium hydride (50% in mineral oil) to a suspension of 2.16 g (0.0075 moles) of (S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (as obtained in step E of Example 1) in 35 ml of anhydrous dimethoxyethane and stir until the evolution of gas ceases. Add dropwise a solution of 0.75 ml of dimethylcarbamyl chloride in 5 ml of anhydrous dimethoxyethane. Stir for 36 hours at room temperature and concentrate to dryness; dissolve the residue in 50 ml of ethyl ether and filter to remove the solid. Wash the filtrate twice with 30 ml of 0.5 N sodium hydroxide, dry the ether layer over anhydrous sodium sulfate, and precipitate (S)-7-chloro-8-dimethylaminocarbonyloxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with 1 N ethereal hydrogen chloride. Obtain an analytical sample by crystallization from 2-propanol, m.p. 261°-263° C. [α]D26 =+23.1° (c=1, dimethylformamide).

Provenance & Evidence