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

HRID 1390987Notes

Reaction equation

HRID 1390987 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

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

Product 1

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-[(4-nitrophenyl)methyl]-4-methylpiperazine (3.5 g, 0.015 M) and 700 mg of 5% Pd/C in 200 ml of absolute ethanol is hydrogenated for 20 minutes. This is then filtered, washed with more ethanol and concentrated to a white oil. This is crystallized from acetate/Skellysolve® B to give 900 mg (30%) of white crystalline 1-methyl-4-[(4-aminophenyl)methyl]piperazine.

Workup

  1. filtrationThis is then filtered
  2. washwashed with more ethanol
  3. concentrationconcentrated to a white oil
  4. customThis is crystallized from acetate/Skellysolve® B

Sources & evidence

ORD record
ord-0695f04e803d4533abb64949b4deddcc
Source dataset
uspto-grants-1979_02
Patent number
US04140775

Reaction notes

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