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

HRID 2232403Notes

Reaction equation

HRID 2232403 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].[H][H]>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

5

Reactant 2

HCID 28651491-Acetyl-4-(4-nitrophenyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-acetyl-4-(4-nitrophenyl)piperazine (28.8 g) in ethanol (400 ml) was hydrogenated at 4 bar in the presence of 10% palladium/carbon (0.5 g) until no further hydrogen was taken up. The catalyst was filtered off and the filtrate was evaporated. The residue was triturated with diethyl ether, filtered and dried to give the title compound (23.8 g), m.p. 142°-144° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-7692e30126f9454f90c0826d46ce0623
Source dataset
uspto-grants-1988_11
Patent number
US04788196

Reaction notes

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