Tetrahydrofuran → 2,2-Dimethyl-N-[2-[2-(3-methyl-2-thienyl)-2-(1-propyl)aminoethyl]phenyl]propanamide

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To a stirred, chilled (-10° C.) solution of 10.14 g of N-[(2-methyl)-phenyl]-2,2-dimethylpropanamide and 80 ml of tetrahydrofuran, was added over 45 min 48 ml of 2.5M n-butyllithium in hexane, maintaining the temperature below 0° C. The solution was stirred for 2 hr, with cooling. To the suspension, was added a solution of 10.6 g of 3-methyl-2-thiophene carboxaldehyde-n-propylimine and 45 ml of tetrahydrofuran, with stirring and cooling over 15 min. The solution was stirred for 1.5 hr, with cooling, and then 150 ml of water was added. The mixture was concentrated. The residue was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the residue was accomplished by Preparative HPLC (Water Associates Prep LC/System 500, silica gel, eluted with ethyl acetate, flow rate 200 ml/min, Gow Mac model 80-800 UV detector). The appropriate fractions were combined and concentrated to give 15.2 g of product, as an oil.

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