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

HRID 2213884Notes

Reaction equation

HRID 2213884 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-fbb11acf807a4a2ab4624599686dd32b
Source dataset
uspto-grants-2006_09
Patent number
US07105670B2

Reaction notes

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