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

HRID 2068532Notes

Reaction equation

HRID 2068532 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].C1(C)C=CC=CC=1>[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

5

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 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Combine benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate (120.0 g, 359.9 mmol) and ethanol (2.0 L) in a Büchi hydrogenator and add 10% palladium on carbon (Pd/C) (10.0 g, 9.4 mmol) slurried in toluene (200 ml). Hydrogenate (60 psi, ambient temperature) the mixture for approximately 64 hours. Filter the mixture through diatomaceous earth and wash the cake with THF (300 ml). Concentrate the filtrate under reduced pressure to give the title compound (60 g, 84%) as a white foam: MS (m/z): 200 (M+1).

Workup

  1. filtrationFilter the mixture through diatomaceous earth
  2. washwash the cake with THF (300 ml)
  3. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-264235354807467690c8822f7bcc0089
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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