HCID 57437918, compound → 1,3-Dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine

HRID 1674490Notes

Reaction equation

HRID 1674490 reaction equation
[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:16])[CH2:3]1.CC1C2C=C([N+]([O-])=O)C=CC=2CCN(C)C1>[Pd].CO>[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:16])[CH2:3]1

Participants

5

Reactant 2

HCID 57437918HCID 57437918, compoundHCID 57437919HCID 57437919, compound

Product 1

HCID 574379201,3-Dimethyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.4 g (6.3 mmol) of a mixture of 1,3-dimethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine and 1,3-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine, 20 ml of methanol and 0.20 g 10% palladium on charcoal is hydrogenated for 5.5 h under a hydrogen atmosphere (50 psi). It is filtered, concentrated and the mixture is purified by chromatography with silica gel (eluant: dichloromethane:95% ethanol/5% ammonia 99:1 to 80:20). 0.45 g of 1,3-dimethyl-7-amino-2,3,4,5-tetrahydro-1H-benzo[d]azepine are obtained

Workup

  1. filtrationIt is filtered
  2. concentrationconcentrated
  3. customthe mixture is purified by chromatography with silica gel (eluant: dichloromethane:95% ethanol/5% ammonia 99:1 to 80:20)

Sources & evidence

ORD record
ord-624ff3fdad324b09acf0cfaf4149064e
Source dataset
uspto-grants-2011_08
Patent number
US08003639B2

Reaction notes

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