1-Methyl-4-(2-methyl-4-nitrophenyl)piperazine → 3-Methyl-4-(4-methylpiperazin-1-yl)aniline

HRID 252018Notes

Reaction equation

HRID 252018 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[CH3:17])[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[CH3:17])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 184397481-Methyl-4-(2-methyl-4-nitrophenyl)piperazine

Product 1

HCID 91152613-Methyl-4-(4-methylpiperazin-1-yl)anilineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A heterogeneous mixture of 4-(4-methylpiperazinyl)-3-methylnitrobenzene 5 (20 g, 85 mmol), 10% Pd/C (1.3 g) in methanol (1.2 liter) was hydrogenated [H2] at 40 PSI for 3 hours. The palladium catalyst was filtered through a pad of celite, washed with methanol (3×50 mL) and the combined filtrate was concentrated to afford 4-(4-methylpiperazinyl)-3-methylaniline 7 (15 g, 86%). 1H NMR (CD3OD): δ 6.83 (d, 1H, J=8.7 Hz), 6.59 (d, 1H, J=2.7 Hz), 6.54 (dd, 1H, J=8.4 and 2.7 Hz), 2.84 (t, 4H, J=4.8 Hz), 2.60 (bm, 4H), 2.34 (s, 3H), 2.20 (s, 3H); LCMS: purity: 99.9%, MS (m/e): 206 (MH+).

Workup

  1. customfor 3 hours
  2. filtrationThe palladium catalyst was filtered through a pad of celite
  3. washwashed with methanol (3×50 mL)
  4. concentrationthe combined filtrate was concentrated

Sources & evidence

ORD record
ord-860ed844ce344a058c7b060b4521137c
Source dataset
uspto-grants-2011_01
Patent number
US07868013B2

Reaction notes

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