1-Methyl-4-(4-nitrobenzyl)piperazine → 4-((4-Methylpiperazin-1-yl)methyl)aniline

HRID 501220Notes

Reaction equation

HRID 501220 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1>CO.[Ni]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 6777951-Methyl-4-(4-nitrobenzyl)piperazine

Product 1

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineYield 91.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-4-(4-nitrobenzyl)piperazine (4.0 g) in methanol (100 mL) at room temperature under nitrogen atmosphere was added Raney nickel (1.6 gm). The reaction mixture was stirred for 2 hr under hydrogen atmosphere. The progress of the reaction was monitored by TLC and upon completion of the reaction, the mixture was filtered under nitrogen atmosphere and the solvent was removed under reduced pressure to give 4-[(4-methylpiperazin-1-yl)methyl]aniline (3.2 g). 1H NMR (CDCl3, 200 MHz) δ: 7.13 (2H, d, J=8.4 Hz), 6.61 (2H, d, J=8.4 Hz), 3.41 (2H, s), 2.45 (8H, bm), 2.27 (3H, s); m/e=206 (M+1).

Workup

  1. customThe progress of the reaction was monitored by TLC and upon completion of the reaction
  2. filtrationthe mixture was filtered under nitrogen atmosphere
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ac0874e7ff6c46658b2fe821ad1c95e2
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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