反应详情

A mixture of 2-aminotetralin (5 g) and 1-[1-(p-toluenesulfonyl)-indol-4-yloxy]-2,3-epoxypropane (11.7 g) in absolute ethanol (150 ml) is refluxed for 6 hours. The solvent is evaporated, the obtained residue is dissolved under stirring in hot isopropanol (100 ml) and the solution is made acidic by the addition of hydrochloric acid in isopropanol. The precipitate which forms is recovered by filtration, dissolved in a mixture of ethanol (250 ml) and aqueous sodium hydroxide (7.6 g in 85 ml of water). The reaction mixture is refluxed for 6 hours, the solvent is evaporated off and the residue is dissolved in ethyl acetate (200 ml). The obtained solution is washed twice with water, dried over sodium sulfate and concentrated by evaporating off the solvent. The residue is chromatographed on a silica gel column eluting with ethyl acetate. The fractions containing pure product are pooled. The solvent is evaporated and the residue is dissolved in ethyl ether (20 ml) and crystallized therefrom yielding 3.5 g of N-(1,2,3,4-tetrahydronaphth- 2-yl)-2-hydroxy-3-(4-indolyloxy)propanamine; m.p. 65°-68° C.

1. temperatureis refluxed for 6 hours
2. customThe solvent is evaporated
3. dissolutionthe obtained residue is dissolved
4. additionthe solution is made acidic by the addition of hydrochloric acid in isopropanol
5. filtrationThe precipitate which forms is recovered by filtration
6. dissolutiondissolved in a mixture of ethanol (250 ml) and aqueous sodium hydroxide (7.6 g in 85 ml of water)
7. temperatureThe reaction mixture is refluxed for 6 hours
8. customthe solvent is evaporated off
9. dissolutionthe residue is dissolved in ethyl acetate (200 ml)
10. washThe obtained solution is washed twice with water
11. dry with materialdried over sodium sulfate
12. concentrationconcentrated
13. customby evaporating off the solvent
14. customThe residue is chromatographed on a silica gel column
15. washeluting with ethyl acetate
16. additionThe fractions containing pure product
17. customThe solvent is evaporated
18. dissolutionthe residue is dissolved in ethyl ether (20 ml)
19. customcrystallized