Tert-butyl 4-(3-fluoro-4-nitrophenyl)piperazine-1-carboxylate → Tert-butyl 4-(4-amino-3-fluorophenyl)piperazine-1-carboxylate

HRID 557749Notes

Reaction equation

HRID 557749 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)=[C:16]([F:23])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[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])=[C:16]([F:23])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 66738172Tert-butyl 4-(3-fluoro-4-nitrophenyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57652076Tert-butyl 4-(4-amino-3-fluorophenyl)piperazine-1-carboxylateYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 4-(3-fluoro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (2.1 g, 6.4 mmol) in ethyl acetate (20 mL) in the presence of 10% palladium on carbon was shaken under the hydrogen with a pressure of 50 psi at room temperature for 2 hr. The reaction mixture was filtered through a plug of celite and the filtration pad was washed with ethyl acetate. The organic layer was collected, concentrated, and dried to give 4-(4-amino-3-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (1.90 g, crude) as a light red solid, which was directly used in the next step reaction without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washthe filtration pad was washed with ethyl acetate
  3. customThe organic layer was collected
  4. concentrationconcentrated
  5. customdried

Sources & evidence

ORD record
ord-4afaa9cce5884e4091defa52a815ee61
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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