Piperazine → N-(6-Methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide

Participants

Reaction Steps

A mixture of 8 g (0.022 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)-hexanamide and 35 g (0.41 mole) of piperazine was stirred at 125° for 1 hr, cooled and suspended in water. The resulting fine precipitate was collected and dissolved in dichloromethane. The solution was washed with water, dried, and concentrated to dryness in vacuo. The residue was chromatographed over 560 g of alumina with 500 ml each of the following solutions of methanol in an ethyl acetate:dichloromethane (1:9) mixture: 2%, 3%, 4%, 5% and 10% to afford 2.6 g of crude product, Rf(alumina--75 parts of ethyl acetate:25 parts of methanol:1 part of triethylamine)=0.38. Recrystallization from toluene afforded 1.9 g (23%) of the title compound, mp 122°-124°.

Provenance & Evidence