2-Chloro-N,N-dimethylethylamine → (cis)-7-Chloro-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-methyl-2H-1-benzazepin-2-one, monohydrochloride

Participants

Reaction Conditions

Reaction Steps

To a slurry of hexane washed sodium hydride (132 mg of 50% sodium hydride in mineral oil, 2.74 mmole) in 20 ml of dimethylformamide at 25° C. was added 720 mg of (cis)-7-chloro-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-methyl-2H-1-benzazepin-2-one (2.28 mmole). After stirring at 25° C. for 1 hour, the solution turned clear, 6.7 ml of a 1.7 M solution of 2-dimethylaminoethyl chloride (11.4 mmole, 5 equiv.) in toluene was added. The reaction mixture was stirred for 3 hours at 80° C., then cooled to 25° C. and quenched with 1N hydrochloric acid, basified with 1N sodium hydroxide, and extracted with ethyl acetate. The organic layer was dried (magnesium sulfate) and concentrated. The residue was diluted with ether and treated with a saturated solution of hydrochloric acid in ether and concentrated. The residue was triturated with ether and filtered. The solid was washed with ether and dried to give 780 mg of the title compound as a white solid, melting point 228°-231° C.

Provenance & Evidence