2-Chloro-N,N-dimethylethylamine → HCID 70083343, compound

Participants

Reaction Steps

A mixture of 3.9 g (0.01 mol) of rac.-cis-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-1, 4-thiazepin-5(4H)-one, 1.5 g of powdered potassium carbonate and 1.3 g (0.011 mol) of 2-dimethylaminoethyl chloride in 100 mL of ethyl acetate was stirred and heated at reflux for 2 hrs, then twice an additional 0.5 g of 2-dimethylaminoethyl chloride was added at 2 hr intervals. The mixture was heated at reflux for a total of 12 hrs, cooled to room temperature and diluted with water. The organic solution was separated, washed with brine, dried (MgSO4) and the solvent was removed under reduced pressure. The residue in acetone was treated with hydrogen chloride (anhydrous) and the crude hydrochloride salt after recrystallization from acetone afforded 4.0 g (80%) of rac.-cis-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-4 -[2-(dimethylamino)ethyl]-3-phenyl-1,4-thiazepin-5(4H)-one hydrochloride, mp 125°-127°.

Provenance & Evidence