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6,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amine → 2-Propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amine

HRID 450742
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 450742
Cl[C:2]1[C:14]2[CH2:13][CH2:12][CH:11]3[CH:7]([CH2:8][N:9]([CH2:15][CH2:16][CH3:17])[CH2:10]3)[C:6]=2[CH:5]=[C:4](Cl)[C:3]=1[NH2:19]>CO.C(OCC)(=O)C.[OH-].[Na+].[OH-].[OH-].[Pd+2]>[CH2:15]([N:9]1[CH2:8][CH:7]2[CH:11]([CH2:12][CH2:13][C:14]3[CH:2]=[C:3]([NH2:19])[CH:4]=[CH:5][C:6]=32)[CH2:10]1)[CH2:16][CH3:17]
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Komponenten

6

Edukt 1

HCID 670239596,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amine

Produkt 1

HCID 670239882-Propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amineAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl Acetate
Lösungsmittel
HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture of 6,8-dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amine (800 mg, 2.67 mmol) and 20% palladiumhydroxide on carbon in methanol (50 ml) was hydrogenated over night at room temperature. The catalyst was filtered, and the solvent was removed under vacuum to yield the crude product. The residue was dissolved in ethyl acetate and 1 M NaOH solution. The aqueous phase was once more extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the pure product (530 mg, 86%).

Aufarbeitung

  1. waitwas hydrogenated over night at room temperature
  2. filtrationThe catalyst was filtered
  3. customthe solvent was removed under vacuum
  4. customto yield the crude product
  5. extractionThe aqueous phase was once more extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f40fa3a684ab448a85524738320ee5ab
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486984B2

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