benzyl N-(1-methyl-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl)carbamate → 1-methyl-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine

HRID 2068544Notes

Reaction equation

HRID 2068544 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:26]=[CH:25][CH:24]=[CH:23][C:8]=3[CH2:9][CH2:10][CH:11]([NH:12]C(=O)OCC3C=CC=CC=3)[C:5]2=[N:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[N:6]2[C:7]3[CH:26]=[CH:25][CH:24]=[CH:23][C:8]=3[CH2:9][CH2:10][CH:11]([NH2:12])[C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 58304076benzyl N-(1-methyl-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 583040471-methyl-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amineYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 702EthanolSolvent

Procedure

Combine benzyl N-(1-methyl-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl)carbamate (0.99 g, 2.85 mmol) and 10% Pd/C (200 mg, 1.88 mmol) in absolute ethanol (50 mL). Place the mixture on a Parr shaker for 7 hours (hydrogen (H2) 60 psi, ambient temperature). Remove the catalyst by filtration, add 10% Pd/C (200 mg, 1.88 mmol) to the filtrate, and place the mixture on a Parr shaker for 7 additional hours (60 psi, ambient temperature). After 7 hours, add more 10% Pd/C (189 mg, 1.78 mmol) and shake for 7 additional hours. Remove the catalyst by filtration and concentrate the filtrate under reduced pressure to give the title compound (0.53 g, 87%): MS (m/z): 214 (M+1).

Workup

  1. customfor 7 hours
  2. customRemove the catalyst
  3. filtrationby filtration
  4. customRemove the catalyst
  5. filtrationby filtration
  6. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-aa7a3eef5bf9440da2bae02c29ea96bb
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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