Sodium Hydroxide → 6-Methoxy-4-methyl-N-[6-(1-piperazinyl)hexyl]-8-quinolinamine

Participants

Reaction Steps

A cold (-40°) slurry of 3.8 g (0.0285 mole) of anhydrous aluminum chloride in 60 ml of tetrahydrofuran was added to an equally cold suspension of 3.2 g (0.087 mole) of lithium aluminum chloride in 40 ml of tetrahydrofuran. The mixture was allowed to warm to -20° and to it was added portionwise a suspension of 7.8 g (0.021 mole) of N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide in 300 ml of tetrahydrofuran. The mixture was allowed to stir overnight as it warmed to room temperature, and then was treated with 13.5 ml of 30% sodium hydroxide solution, and with enough water to clarify the supernatant. The supernatant was separated from the sticky precipiate, concentrated in vacuo to remove most of the tetrahydrofuran, diluted with dichloromethane, washed with water, dried and concentrated to dryness in vacuo. The residue was chromatographed over 200 g of silica gel first with 1 liter of ethyl acetate and then with the following solutions of methanol in ethyl acetate: 5% (1 liter), 10% (1 liter), 15% (1 liter), 20% (1 liter) and 25% (4 liters). The eluant containing product, Rf(silica--75 parts ethyl acetate:25 parts of methanol:1 part triethylamine)=0.05, was concentrated to dryness in vacuo to afford 4.4 g (59%) of the desired product of sufficient purity to use in the next step.

Provenance & Evidence