A mixture of 6 g (0.0164 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide, 3 g (0.017 mole) of 1-(3-methyl-butyl)-3-methylpiperazine and 3 ml of triethylamine in 100 ml of benzene was heated under reflux for 30 hr, allowed to cool and filtered to remove triethylamine hydrobromide. The filtrate was combined with 1 ml of triethylamine and heated under reflux for 28 hr. The cooled reaction mixture was combined with water and additional benzene. The benzene layer was separated, washed, dried and concentrated to dryness. The residue dissolved in ethyl acetate and chromatographed over 200 g of silica gel first with ethyl acetate, then with a 7% solution of methanol in ethyl acetate and finally with a 10% solution of methanol in ethyl acetate. Fractions containing product, Rf (15% methanol/ethyl acetate)=0.12, were combined and concentrated to afford 3.3 g (44%) of the desired product as an oil, which was used in the next step without further purification. The structure was confirmed by IR and NMR spectra.
