3-Azido-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine-2-one → racemic 3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine

HRID 2257513Notes

Reaction equation

HRID 2257513 reaction equation
[N:1]([CH:4]1[C:10](=O)[N:9]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:5]1)=[N+]=[N-]>C(O)C.C1COCC1.[Pd]>[NH2:1][C:4]1[N:5]=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2[N:9]([CH2:12][C:13]([F:16])([F:14])[F:15])[CH:10]=1

Participants

5

Reactant 1

HCID 189689903-Azido-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine-2-one

Product 1

HCID 18968926racemic 3-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepineYield 75.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3-Azido-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine (83.4 mmol ,30 g) in 300 mL ethanol and 150 mL THF was added 10% Pd/C (10 wt %, 3.0 g). Hydrogen gas was bubbled through the solution for 8 h. The reaction was filtered and evaporated under reduced pressure. The residue was crystallized from ethyl ether to give 20.0 g of white crystals. Another 4 g was recovered from evaporation and recrystallization of the filtrates. Combined yield, 86.7%.

Workup

  1. customHydrogen gas was bubbled through the solution for 8 h
  2. filtrationThe reaction was filtered
  3. customevaporated under reduced pressure
  4. customThe residue was crystallized from ethyl ether

Sources & evidence

ORD record
ord-a57f76f0cbd94038a28026cfe176ac2a
Source dataset
uspto-grants-1997_08
Patent number
US05658901

Reaction notes

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