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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
Notes
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Reaction equation

HRID 450742 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 1

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

Product 1

HCID 670239882-Propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amineYield 86.2%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl Acetate
Solvent
HCID 14798Sodium HydroxideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-f40fa3a684ab448a85524738320ee5ab
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486984B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes