1,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-one → 3-(4-Aminophenyl)-1,4-dimethylpiperazin-2-one

HRID 888425Notes

Reaction equation

HRID 888425 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C:3]1=[O:18]>[Pd].C(O)C>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH:4]2[N:5]([CH3:8])[CH2:6][CH2:7][N:2]([CH3:1])[C:3]2=[O:18])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 576250981,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-one

Product 1

HCID 576251203-(4-Aminophenyl)-1,4-dimethylpiperazin-2-oneYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 3 (200 mg, 0.80 mmol), ethanol (5 mL) and 10% palladium on carbon (50% wet, 4 mg dry weight). The reaction flask was purged with hydrogen gas and the reaction mixture stirred under a balloon pressure of hydrogen for 2 h. After this time the flask was purged with nitrogen. The catalyst was removed by filtration through a pad of Celite 521 and the filter cake washed with ethanol (10 mL). The filtrate was concentrated under reduced pressure to afford a 94% yield of 4 (166 mg) as a colorless oil: 1H NMR (500 MHz, DMSO-d6) δ 6.89 (d, 2H, T=8.5 Hz), 6.47 (d, 2H, J=8.5 Hz), 4.94 (s, 2H), 3.53 (td, 1H, J=12.0, 4.0 Hz), 3.44 (m, 1H), 3.21 (dt, 1H, J=12.0, 4.0 Hz), 2.92 (dt, 1H, J=12.0, 4.0 Hz), 2.82 (s, 3H), 2.02 (s, 3H); MS (ESI+) m/z 220 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customThe reaction flask was purged with hydrogen gas
  4. customAfter this time the flask was purged with nitrogen
  5. customThe catalyst was removed by filtration through a pad of Celite 521
  6. washthe filter cake washed with ethanol (10 mL)
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bcc9ff683d4a4dda80001fe76a17636f
Source dataset
uspto-grants-2012_08
Patent number
US08247550B2

Reaction notes

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