2-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione → 2-(1,1-dimethyl-2-propenyl)-1H-indole-3-ethanamine

HRID 1356287Notes

Reaction equation

HRID 1356287 reaction equation
[CH3:1][C:2]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][N:17]1C(=O)C3C(=CC=CC=3)C1=O)=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:5])[CH:3]=[CH2:4]>CO.C(Cl)Cl>[CH3:5][C:2]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][NH2:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:1])[CH:3]=[CH2:4]

Participants

3

Reactant 1

HCID 223969612-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 223967402-(1,1-dimethyl-2-propenyl)-1H-indole-3-ethanamine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione (1.10 g, 3.07 mmol) in 3:1 MeOH/CH2Cl2 (20 mL) at rt under argon was added N2H4.H2O (0.52 mL). The reaction mixture was stirred overnight, concentrated in vacuo, diluted with CHCl3, then extracted with H2O. The CHCl3 layer was separated. The H2O layer was extracted further with CHCl3. The combined CHCl3 extracts were washed, dried, filtered, and concentrated to give the title compound: MS (ESI+) m/z 229.2.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with CHCl3
  3. extractionextracted with H2O
  4. customThe CHCl3 layer was separated
  5. extractionThe H2O layer was extracted further with CHCl3
  6. washThe combined CHCl3 extracts were washed
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b5a35fac81384c339d5360076e6dfcda
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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