The Synthesis of Medetomidine and Its Naphtalenic Derivative

A two step method (consisting of transformation of aldehyde to alcohol and substitution of imidazole group) was used for the synthesis of naphtalenic derivative of medetomidine and the optimized conditions were then applied to the synthesis of medetomidine. Thus, after optimization of first step (preparation of chiral alcohol), the various reaction parameters that affect the yield of naphtalenic derivative of medetomidine following second step were determined. Then produced alcohol was treated by TMS-imidazole in the presence titanium tetrachloride in anhydrous chloroform and the reaction mixture is worked up of by two step addition of sodium hydroxide. The same conditions applied in the synthesis of medetomidine, has afforded the same result (99% yield).

Keywords:

Medetomidine , TMS-imidazole , naphtalenic , 1-(naphthalen-1-yl)ethanol