Hydrochloric Acid → HCID 21250998, compound

Participants

Reaction Conditions

Reaction Steps

2.7 ml of a solution of hydrochloric acid (0.5 N) in isopropanol are slowly added, at 0° C. to a solution of 0.5 g (1.32 mmol) of 1-(2-methoxyphenyl)-2-[[1-(phenylmethyl)piperidin-4-yl]methoxy]-1H-imidazole in 15 ml of dichloromethane. The solvents are removed by evaporation and then the product is taken up in 15 ml of dichloromethane. The solution is cooled to −15° C. and 1.05 ml of boron tribromide is slowly added. The reaction medium is stirred for 3 h 30 min while allowing the temperature to return to 20° C. The reaction mixture is poured over ice and sodium bicarbonate is added until a pH=8 is obtained. After separating upon settling out, the aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with water and then with brine. The medium is dried over magnesium sulphate, filtered and concentrated. The expected compound is purified on a silica gel, eluting with a 99:1 to 93:7 CH2Cl2/CH3OH mixture. 0.355 g of product is obtained. (Yield 74%)

Provenance & Evidence