反应详情

A mixture of 6.0 g (0.0195 mole) of N-(6-chlorohexyl)-6-methoxy-4-methyl-8-quinolinamine and 6 ml of 1-piperazinecarboxylic acid, ethyl ester in 2 ml of toluene was heated in an oil bath at 135° for 3 hr, allowed to cool, diluted with ethyl acetate and toluene, washed with water, dried, and concentrated to dryness in vacuo. The residue was chromatographed over 700 g of silica gel first with 2 l of ethyl acetate and then with 2 l each of the following solutions of methanol in ethyl acetate: 2%, 5%, 10%, and 20%. The eluant containing product, Rf (silica--ethyl acetate)=0.16, was concentrated to dryness. The residue was taken up in ether, filtered to remove dark flocculent material, and then treated with 1.2 ml of 85% phosphoric acid in 30 ml of ethanol. The gum which settled was washed with ether and acetone and then dissolved in 2-propanol and water. The pH of the solution was adjusted to 8 with ammonium hydroxide. The solution was then heated on the steambath, diluted with water to the cloud point and chilled to afford 1.7 g (21%) of the title compound, mp. 59°-60°.

1. temperaturewas heated in an oil bath at 135° for 3 hr
2. temperatureto cool
3. washwashed with water
4. customdried
5. concentrationconcentrated to dryness in vacuo
6. customThe residue was chromatographed over 700 g of silica gel first with 2 l of ethyl acetate
7. additionThe eluant containing product, Rf (silica--ethyl acetate)=0.16
8. concentrationwas concentrated to dryness
9. filtrationfiltered
10. customto remove dark flocculent material
11. additiontreated with 1.2 ml of 85% phosphoric acid in 30 ml of ethanol
12. washThe gum which settled was washed with ether and acetone
13. dissolutiondissolved in 2-propanol
14. temperatureThe solution was then heated on the steambath
15. additiondiluted with water to the cloud point
16. temperaturechilled