2-Chloro-N,N-dimethylethylamine → HCID 131716585, compound

Participants

Reaction Steps

A mixture of 1.7 g (0.0044 mol) of cis-rac.-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-2-phenyl-1,4-thiazepin-5(4H)-one, 0.7 g (0.005 mol) of powdered potassium carbonate and 0.6 g (0.0049 mol) of 2-dimethylaminoethyl chloride in 30 ml of ethyl acetate was stirred at reflux for 2 hours, then twice an additional 0.2 g of dimethylaminoethyl chloride was added at 2 hour intervals. The mixture was heated at reflux for a total of 12 hours, then cooled to room temperature and diluted with water. The organic solution was separated, washed with brine then dried (MgSO4) and the solvent was removed under reduced pressure. The residue was dissolved in acetone and passed through a 10 g silica gel pad which was washed with acetone (12×30 ml). The solvent was evaporated to give 1.8 g (0.039 mol) of crude base which was dissolved in acetone and 0.5 g (0.04 mol) of fumaric acid was added. The resulting crystals were collected to give 1.1 g (44%) cis-rac.-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-4-[2-(dimethylamino)ethyl]-2-phenyl-1,4-thiazepin-5(4H)-one (E)-2-butenedioate, mp 176°-177°.

Provenance & Evidence