N,N-Dimethylethylenediamine → N-[2-(dimethylamino)ethyl]-2-(5-methYl-2-thienyl)-4-quinolinamine

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A solution of N,N-dimethylethylenediamine (0.66 ml, 6.0 mmol) in ether (15 mL) was treated with a commercial solution of n-butyllithium (6.0 mmol) in hexanes at -10° C., and the resultant mixture was stirred at -10° C. for 20 minutes before treatment with a solution of ketimine 12q (0.42 g, 1.5 mmol) in ether (5 mL). The mixture was stirred at -10° C. for an additional 45 minutes, and then quenched with water (0.5 mL). The organic layer was concentrated on a rotary evaporator to give a crystalline residue. Removal of colored polymeric materials on a short silica gel column by eluting quinoline 9g with hexanes/Et3N/EtOH (7:2:1) was followed by crystallization of the purified 9g from hexanes; yield 82%, mp 103°-105° C.

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