Methyl iodide → Cgp-20712

Participants

Reaction Steps

0.48 g of potassium tert.-butoxide is added while stirring in an ice bath to a solution of 1 g of the 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol obtained according to Example 3 in 20 ml of dimethylformamide. After 10 minutes, a solution of 0.3 g of methyl iodide in 1 ml of dimethylformamide is added dropwise over a period of 20 minutes. The mixture is then stirred for 2 hours at room temperature, the solvent is removed in a rotary evaporator and the residue is chromatographed on silica gel with a solvent mixture of chloroform/methanol/ammonia (700:50:1), yielding the two isomeric compounds 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol having a melting point of 195°-197° and 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol having a melting point of 157°-159°.

Provenance & Evidence