Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate → tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylate

HRID 513284

Reaction equation

HRID 513284 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CCO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 22330126Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 22330182tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate in EtOH (20 mL) and THF (10 mL) was added Pd/C (500 mg), the mixture was charged with H2 (1 atm) and stirred for 16 h. Pd/C was filtered off, the filtrate was concentrated to give tert-butyl 4-(3-aminophenyl)piperazine-1-carboxylate (1.71 g).

Workup

  1. additionthe mixture was charged with H2 (1 atm)
  2. filtrationPd/C was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1ed4b68bf7e8475f86a60a9f5e6fa90a
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Linked notes

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