Ethanol → (R)-5,6-Dihydro-4H-benzo[F]imidazo[1,2-A]azepin-4-amine

HRID 2068538Notes

Reaction equation

HRID 2068538 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:25]=[CH:24][CH:23]=[CH:22][C:7]=3[CH2:8][CH2:9][C@@H:10]([NH:11]C(=O)OCC3C=CC=CC=3)[C:4]2=[N:3][CH:2]=1.C(O)C>[Pd]>[CH:1]1[N:5]2[C:6]3[CH:25]=[CH:24][CH:23]=[CH:22][C:7]=3[CH2:8][CH2:9][C@@H:10]([NH2:11])[C:4]2=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 58304077benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate

Product 1

HCID 58304055(R)-5,6-Dihydro-4H-benzo[F]imidazo[1,2-A]azepin-4-amineYield 100.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Dissolve benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate (6.95 g, 20.85 mmol) in absolute ethanol (375 mL, 6.44 moles) and add 10% palladium on carbon (Pd/C) (0.70 g, 6.57 mmol). Place the mixture on a Parr shaker under Hydrogen (H2) for 7 hours (60 psi, ambient temperature). Remove the catalyst by filtration and concentrate the filtrate under reduced pressure to give the title compound (4.17 g, 100%) as a yellow solid: MS (m/z): 200 (M+1).

Workup

  1. customfor 7 hours
  2. custom(60 psi, ambient temperature)
  3. customRemove the catalyst
  4. filtrationby filtration
  5. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-db1c66b637034b93b8e2d09dda25272c
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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