tert-Butyl 4-(4-nitrophenyl)-1,4-diazepane-1-carboxylate → Tert-butyl 4-(4-aminophenyl)-1,4-diazepane-1-carboxylate

HRID 1509869Notes

Reaction equation

HRID 1509869 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18008978tert-Butyl 4-(4-nitrophenyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 18008968Tert-butyl 4-(4-aminophenyl)-1,4-diazepane-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-Nitro-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3.6 g) was diluted with ethanol (50 mL) and 10% Pd/C (400 mg) was added. The mixture was placed on a Parr shaker for hydrogenation at 50 psi for 3 hr The mixture was filtered and the solvent was removed to afford 4-(4-amino-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3.2 g, 99% yield) as amorphous purple semi-solid. ES-MS for C16H25N3O2 calcd. (m/e) 291, observed 292 (M+H).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-699356c9bf54430d802e0253f749d8cf
Source dataset
uspto-grants-2012_07
Patent number
US08211884B2

Reaction notes

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