Iodine → 1-[2-(Dimethylamino)-1-[4-(phenylmethoxy)phenyl]ethyl]cyclohexanol

Participants

Reaction Conditions

Reaction Steps

Activated magnesium turnings (8 g) and a few crystals of iodine were charged to diethyl ether (200 ml). After addition of 1,5-dibromopentane (20.7 ml; 0.15 mol), the reaction mixture was refluxed for 2 hours. The reaction mass was cooled to 0-5° C. Separately prepared solution of 2-(4-benzyloxy-phenyl)-3-dimethylamino-propionic acid methyl ester (10 g; 0.032 mol) in diethyl ether (100 ml) was added to the above reaction mass very slowly. The temperature was raised to 25-30° C. with constant stirring for 2 hours. After completion of the reaction; the reaction mass was quenched with saturated ammonium chloride solution (100 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml) and the combined organic layer was washed with water (100 ml). The organic layer was dried on sodium sulphate, concentrated under reduced pressure and the product was isolated in n-heptane (25-30 ml). The material was dried under vacuum at 45-50° C. Yield: 7 g, Efficiency: 62%.

Provenance & Evidence