tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate → 1,1-Dimethylethyl 4-(4-amino-2-fluorophenyl)-1-piperazinecarboxylate

HRID 2196182Notes

Reaction equation

HRID 2196182 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=2[F:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=2[F:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 16203508tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 162036301,1-Dimethylethyl 4-(4-amino-2-fluorophenyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(2-fluoro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (9.30 g, 28.6 mmol) in EtOH (80 mL) was treated with hydrogen (H2, 50 psi) in the presence of 10% Pd/C (0.50 g). After 2.5 h, the reaction mixture was filtered and the filtrate was concentrated to yield the title compound.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dc83885e5ab64e3ca5d0f8b5e74aef98
Source dataset
uspto-grants-2012_12
Patent number
US08338426B2

Reaction notes

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