Acetic Acid → HCID 22390432, compound

Participants

Reaction Conditions

Reaction Steps

3.46 g of sodium iodide are added, under an inert atmosphere, to 3.68 g of 2-{2-chloro-4-[3-(1-azepanyl)prop-1-ynyl]phenyl}adamantan-2-ol (compound I′.1) in 20 ml of acetonitrile and 10 ml of dichloromethane, followed by 2.35 ml of chlorotrimethylsilane. The reaction mixture is stirred for 2 hours at 30° C., and then 1.06 ml of acetic acid are added, followed by 10 ml of acetonitrile and then 1.81 g of powdered zinc. The reaction mixture is heated at 80° C. for 3 hours, allowed to cool to room temperature, filtered and washed with diethyl ether. The organic phases are dried over sodium sulphate, and then the solvents are evaporated off under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with an 87.5/12.5 (v/v) cyclohexane/ethyl acetate mixture; m.p.=218° C. (HCl).

Provenance & Evidence