Ethanol → 7-Ethoxycarbonylmethyl-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1003712노트

반응식

HRID 1003712 반응식
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:24][CH:23]=3)[CH2:13]2)=[CH:8][CH:7]=1)=[O:4].S(=O)(=O)(O)O.[CH2:40](O)C>>[CH2:1]([O:2][C:3]([CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][CH:27]=3)[CH2:13]2)=[CH:8][CH:7]=1)=[O:4])[CH3:40]

참가 물질

4

반응물 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 187970057-Methoxycarbonylmethyl-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 187970587-Ethoxycarbonylmethyl-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline수율 56%

실험 절차

A stirred, ice-cooled solution of 7-methoxycarbonylmethyl-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (0.202 g, 0.46 mmol) in ethanol (10 ml) was treated with concentrated sulfuric acid (0.53 ml, 0.53 mmol). The mixture was heated at reflux for 2 h. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate (30 ml) and saturated aqueous sodium bicarbonate solution (30 ml). The organic phase was separated and washed with brine. Drying (Na2SO4) and evaporation in vacuo afforded an orange oil which was chromatographed on silica using 50-100% ethyl acetate-pentane gradient elution to afford the title compound as a colourless oil (120 mg, 56%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  5. customThe organic phase was separated
  6. washwashed with brine
  7. customDrying
  8. custom(Na2SO4) and evaporation in vacuo
  9. customafforded an orange oil which
  10. customwas chromatographed on silica using 50-100% ethyl acetate-pentane gradient elution

출처 및 근거

ORD 기록
ord-48c393a013d14f1784057f1a9b6b924d
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046210

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