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 1356287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356287
[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]

Komponenten

3

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b5a35fac81384c339d5360076e6dfcda
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586421B2

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