Potassium Carbonate → 6-Methoxy-8-{4-[1-(quinolin-8-ylmethyl)piperidin-4-yl]piperazin-1-yl}quinoline

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-methoxy-8-(4-piperidin-4-ylpiperazin-1-yl)quinoline (Step 2, 0.06 g) and 8-(bromo)methylquinoline (commercially available, 0.055 g) in anhydrous dimethylsulfoxide (5 mL) was added anhydrous K2CO3 (0.051 g). The resulting mixture was stirred at 70° C. for 18 hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with water and brine and was then dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator to give the desired product, which was converted to its dihydrochloride salt in CH2Cl2 using 1N HCl/Et2O to give 0.31 g of a light yellow solid; MS (ES) m/z (relative intensity); 468 (M+H)+ (100).

Provenance & Evidence