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

HRID 1410482Notes

Reaction equation

HRID 1410482 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][CH:9]=2)[CH2:4][CH2:3]1.[H][H]>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][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 7372534-(4-Methylpiperazin-1-yl)anilineYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-methyl-4-(4-nitrophenyl)piperazine (1.03 g, 4.66 mmol) in MeOH (100 ml) was hydrogenated at 20° C. at atmospheric pressure using an H-Cube (flow rate at 1 ml/min and full hydrogen mode) using a Pd/C cartridge. The solvent was removed in vacuo to afford 4-(4-methylpiperazin-1-yl)benzenamine (0.82 g, 4.29 mmol, 92%) as an off-white solid. 1H NMR (CDCl3) 2.37 (3H, s), 2.62 (4H, t), 3.09 (4H, t), 3.40 (2H, br. s), 6.65 (2H, d), 6.82 (2H, d). LCMS (1) Rt: 0.98 min; m/z (ES+) 192.

Workup

  1. customwas hydrogenated at 20° C. at atmospheric pressure
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-191362e5d2b3483caebde3948a3c9b96
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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