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

HRID 639369Notes

Reaction equation

HRID 639369 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>CO.[Ni]>[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

4

Reactant 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 7372534-(4-Methylpiperazin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

44.3 g (0.2 Mol) of 1-Methyl-4-(4-nitro-phenyl)-piperazine is dissolved in 1200 mL of CH3OH and subjected to catalytic hydration at rt using Raney-Ni (10 g) as catalyst. After filtration over Celite, the crude product is purified via solid-distillation (0.16 mbar, 180° C.; heat temp 125° C.) to obtain 4-(4-methyl-piperazin-1-yl)-phenylamine. Title compound: ES-MS: 192.1 [M+H]+; single peak at tR=1.08 min (System 1); Rf=0.33 (CH2Cl2/MeOH 4:1).

Workup

  1. customsubjected to catalytic hydration at rt
  2. filtrationAfter filtration over Celite
  3. distillationthe crude product is purified via solid-distillation (0.16 mbar, 180° C.; heat temp 125° C.)

Sources & evidence

ORD record
ord-23e97c0f3bb240838aad93102320f6a3
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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