2-Aminotetralin → N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(4-indolyloxy)propanamine

HRID 1656613노트

반응식

HRID 1656613 반응식
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C1(C)C=CC(S([N:21]2[C:29]3[C:24](=[C:25]([O:30][CH2:31][CH:32]4[O:34][CH2:33]4)[CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)(=O)=O)=CC=1>C(O)C>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH2:11][CH:2]1[NH:1][CH2:33][CH:32]([OH:34])[CH2:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[CH:23]=[CH:22][NH:21]2

참가 물질

4

반응물 2

HCID 346772-AminotetralinHCID 13938676glycidyl N-tosyl-4-indolyl ether

생성물 1

HCID 14750933N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(4-indolyloxy)propanamine수율 30.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-28f3b66ba3664289950751ee02bbfea1
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254595

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