Sodium Hydroxide → 8-Quinolinamine, 4-methyl-

A mixture of 2.6 g of crude 4-cyclohexyl-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexanamide in 100 ml of tetrahydrofuran was filtered to remove 0.3 g of white insoluble material. The filtrate, now containing 2.3 g (0.005 mole) of starting material was added dropwise to a cold (-20°) mixture of aluminum chloride and lithium aluminum hydride which had been prepared by adding a cold (-40°) slurry of 1.1 g (0.008 mole) of aluminum chloride in 75 ml of tetrahydrofuran to an equally cold suspension of 0.9 g (0.02 mole) of lithium aluminum hydride in 50 ml of tetrahydrofuran and allowing the mixture to warm to -20°. The reaction mixture was stirred at -20° to 0° for 3 hr and allowed to stand overnight at 4°. To the stirred mixture was added 3.8 ml of 30% sodium hydroxide and enough water to clarify the supernatant, which was then decanted. The residual sticky precipitate was washed with tetrahydrofuran. The supernatant and wash were combined, concentrated in vacuo to remove most of the tetrahydrofuran and taken up in water and ether. The ether layer was washed, dried and concentrated, leaving 2 g of crude product. Recrystallization from 2-propanol afforded 0.9 g (43%) of the purified material, mp 68°-70°.

1. filtrationwas filtered
2. customto remove 0.3 g of white insoluble material
3. customhad been prepared
4. temperatureto warm to -20°
5. waitto stand overnight at 4°
6. customwas then decanted
7. washThe residual sticky precipitate was washed with tetrahydrofuran
8. washThe supernatant and wash
9. concentrationconcentrated in vacuo
10. customto remove most of the tetrahydrofuran
11. washThe ether layer was washed
12. customdried
13. concentrationconcentrated
14. customleaving 2 g of crude product
15. customRecrystallization from 2-propanol

ORD record

ord-2d53355ce84c4793aebd45b59bf6d493

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04659708