(4aRS,5SR,8aRS)-1-Benzyl-5-(benzylamino)perhydroquinoxaline-2,3-dione → (4aRS,5SR,8aRS)-5-amino-1-benzylperhydroquinoxaline-2,3-dione

HRID 1876799

Reaction equation

HRID 1876799 reaction equation
[CH2:1]([N:8]1[CH:17]2[CH:12]([CH:13]([NH:18]CC3C=CC=CC=3)[CH2:14][CH2:15][CH2:16]2)[NH:11][C:10](=[O:26])[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[NH2:18][CH:13]1[CH2:14][CH2:15][CH2:16][CH:17]2[CH:12]1[NH:11][C:10](=[O:26])[C:9](=[O:27])[N:8]2[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68775989(4aRS,5SR,8aRS)-1-Benzyl-5-(benzylamino)perhydroquinoxaline-2,3-dione

Product 1

HCID 68777664(4aRS,5SR,8aRS)-5-amino-1-benzylperhydroquinoxaline-2,3-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(4aRS,5SR,8aRS)-1-Benzyl-5-(benzylamino)perhydroquinoxaline-2,3-dione (1.19 g, 3.28 mmol) was dissolved in methanol (40 ml) and NH4HCO2 (2.07 g, 32.8 mmol) was added. 120 mg of palladium-on-carbon (Merck) was furthermore added. The mixture was heated under reflux for 2 hours. The catalyst was then filtered off and the mixture was evaporated in vacuo. The residue was taken up in CH2Cl2 and the mixture was washed three times with 0.1 N NaOH. The organic phase was dried over Na2SO4 and evaporated in vacuo. A colorless solid was obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe catalyst was then filtered off
  4. customthe mixture was evaporated in vacuo
  5. washthe mixture was washed three times with 0.1 N NaOH
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated in vacuo
  8. customA colorless solid was obtained

Sources & evidence

ORD record
ord-d09017786fd64c849cb81b4d421530a0
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Linked notes

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