1-Acetyl-4-(4-nitrophenyl)piperazine → 1-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

HRID 10779

Reaction equation

HRID 10779 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 28651491-Acetyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneYield 63.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-acetyl-4-(4-nitrophenyl)piperazine (1.8 g, 7.2 mmol) (from Step A above) and 10% palladium-on-charcoal in ethanol (50 mL) was hydrogenated at room temperature and atmospheric pressure overnight. The catalyst was filtered off and the filter cake washed thoroughly with ethanol. The mixture was evaporated under reduced pressure to give 1-acetyl-4-(4-amino-phenyl)piperazine (1.0 g, 63%) as an off-white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. customatmospheric pressure overnight
  3. filtrationThe catalyst was filtered off
  4. washthe filter cake washed thoroughly with ethanol
  5. customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c84ff7750f7042e88d7b296e98f6f5f4
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Linked notes

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