Ethanol → tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

HRID 751591Notes

Reaction equation

HRID 751591 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].C(O)C>[Pd].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

5

Reactant 2

HCID 702EthanolHCID 33806961-Boc-4-(4-Nitrophenyl)piperazine

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (11) (18.9 mmol), 10% palladium-on-carbon (600 mg), ethanol (100 mL), and ethyl acetate (100 mL) is hydrogenated at room temperature and 40 psi for 2 hrs. The mixture is filtered through celite, washing with ethyl acetate (2×100 mL), and concentrated in vacuo to give 4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (12) as a brown oil.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe mixture is filtered through celite
  3. washwashing with ethyl acetate (2×100 mL)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e6449432c9f48c2880418c23795164b
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

Loading…