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

HRID 1003712Notes

Reaction equation

HRID 1003712 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-48c393a013d14f1784057f1a9b6b924d
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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