Sodium Hydroxide → HCID 13077546, compound

Participants

Reaction Steps

A cold (-40°) slurry of 1.7 g (0.0127 mole) of anhydrous aluminum chloride in 50 ml of tetrahydrofuran was added to an equally cold suspension of 1.35 g (0.0355 mole) of lithium aluminum hydride in 30 ml of tetrahydrofuran. The mixture was stirred and allowed to warm to -10°. A solution of 3.3 g (0.0073 mole) of N-(6-methoxy-4-methyl-8-quinolinyl)-6-[4-(2-pyridinyl)-1-piperazinyl]hexanamide, 0.2 hydrate in 100 ml of tetrahydrofuran was added to the mixture dropwise, with stirring. The mixture was stirred for 3 hr, treated with 6.5 ml of 30% sodium hydroxide solution and with enough water to clarify the supernatant, and filtered through Supercel. The filtrate was concentrated in vacuo to remove most of the tetrahydrofuran, diluted with dichloromethane, washed with water, dried and concentrated to dryness. Recrystallization of the residue from 2-propanol afforded 2.1 g (66%) of the title compound, mp 78°-81° .

Provenance & Evidence