1-Methyl-4-(3-nitrophenyl)piperazine → 3-(4-Methylpiperazin-1-yl)aniline

HRID 2375873Notes

Reaction equation

HRID 2375873 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 121521611-Methyl-4-(3-nitrophenyl)piperazine

Product 1

HCID 115646133-(4-Methylpiperazin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into the solution of 1-methyl-4-(3-nitrophenyl)-piperazine (123 mg, 0.556 mmol) in ethanol (5 mL) was added Pd (10% on carbon, 12.0 mg). The mixture was degassed for 5 min and was then was stirred under H2 atmosphere (balloon pressure) at rt for 24 h. After that time, the reaction mixture was filtered and the filtrate was concentrated in vacuo to obtain the title compound as light yellow oil. 1H NMR (CDCl3, 400 MHz): δ=2.35 (s, 3H), 2.56 (t, 41H, J=5.2 Hz), 3.18 (t, 41H, J=5.0 Hz), 3.60 (brs, 2H), 6.21-6.23 (m, 1H), 6.27 (t, 1H, J=2.2 Hz), 6.36-6.39 (m, 1H), 7.05 (m, 1H). MS (ES+): m/z 192.31 (100) [MH+]. HPLC: tR=0.39 min (ZQ2000, polar—5 min).

Workup

  1. customThe mixture was degassed for 5 min
  2. filtrationAfter that time, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-66ba7b7e16044149ba0d324c7698fe88
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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