反应详情

A mixture of 5.5 g (0.015 mole) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide and 1.85 ml (0.018 mole) of 2,6-dimethylmorpholine in 90 ml of benzene was heated under reflux for 24 hr. Triethylamine (2 ml) was added and the mixture was heated under reflux for an additional 2 hr, allowed to cool, and filtered. The filtrate was washed with water, dried and concentrated. TLC(silica gel--ethyl acetate) demonstrated a mixture of the unchanged bromo compound, Rf(silica--ethyl acetate)=0.63, and the product, Rf=0.08. A solution of the residue, 1.3 ml (0.01 mole) of 2,6-dimethylmorpholine, and 1.5 ml of triethylamine in 80 ml of benzene was heated under reflux for 40 hr, allowed to cool, filtered, washed with water, dried and concentrated. The residue was chromatographed over 200 g of silica gel with 1 liter each of the following solutions of methanol in ethyl acetate: 1.5%, 2%, 3% to afford 3.7 g of crude product. Recrystallization from hexane afforded 3.3 g of the title compound, mp 87°-90°. The NMR spectrum confirmed the presence of hexane.

1. temperaturewas heated
2. temperatureunder reflux for 24 hr
3. temperaturethe mixture was heated
4. temperatureunder reflux for an additional 2 hr
5. temperatureto cool
6. filtrationfiltered
7. washThe filtrate was washed with water
8. customdried
9. concentrationconcentrated
10. additiona mixture of the unchanged bromo compound, Rf(silica--ethyl acetate)=0.63
11. temperatureunder reflux for 40 hr
12. temperatureto cool
13. filtrationfiltered
14. washwashed with water
15. customdried
16. concentrationconcentrated
17. customThe residue was chromatographed over 200 g of silica gel with 1 liter each of the following solutions of methanol in ethyl acetate
18. custom1.5%, 2%, 3% to afford 3.7 g of crude product
19. customRecrystallization from hexane