4-Chlorobenzo[g]quinoline (7b) (50 mg, 0.23 mmol), 4-(1-piperidino) aniline (50 mg, 1.2 equivalents), bis(1,5-cyclooctadiene)nickel(O) (Ni(COD)2 1.5 mg, 0.02 equivalents), 1,1′-bis(diphenylphosphino)ferrocene (DPPF, 5 mg, 0.04 equivalents) and sodium t-butoxide (31 mg, 1.4 equiv) in 2.5 mL of dry toluene were refluxed under a 5 nitrogen atmosphere until observed complete by TLC. The mixture was concentrated in vacuo and purified by flash chromatography (gradient: 50:50:2 to 60:40:2 hexane: EtOAc:Et3N) to provide 69 mg of clean N-[4-(1-piperidinyl)phenyl]benzo[g]quinolin-4-amine (8), 85% yield.
