1-Boc-4-(4-Nitrophenyl)piperazine → tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

HRID 557728Notes

Reaction equation

HRID 557728 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][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 33806961-Boc-4-(4-Nitrophenyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (3 g, 9.76 mmol) and 10% palladium on carbon (300 mg) in 50 mL ethanol and 20 mL ethyl acetate was hydrogenated at room temperature under a 50 psi hydrogen atmosphere for 2 hrs. The reaction mixture was filtered through a plug of Celite and evaporated under reduced pressure to give 4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester that was used in the in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5754f8080df0404192c7a5848b49076d
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

Loading…