Methanol → 4-((4-Methylpiperazin-1-yl)methyl)aniline

HRID 1262008Notes

Reaction equation

HRID 1262008 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.[H][H]>[Pd]>[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

5

Reactant 3

HCID 887MethanolHCID 6777951-Methyl-4-(4-nitrobenzyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineYield 93.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-Methyl-4-(4-nitro-benzyl)-piperazine (3.70 g, 15.7 mmol) was dissolved in Methanol (40.0 mL, 987 mmol) and was carefully added to a Parr vessel containing 10% Palladium on Carbon (1.00 g, 74.9 mmol) under nitrogen. The mixture was then placed on a Parr hydrogenation apparatus and was allowed to shake at 55 psi until uptake of hydrogen ceased. The catalyst was then filtered to afford 3.00 g of 4-(4-Methyl-piperazin-1-ylmethyl)-phenylamine without further purification. (M+H)=205.96.

Workup

  1. additionwas carefully added to a Parr vessel
  2. filtrationThe catalyst was then filtered

Sources & evidence

ORD record
ord-572758cd5f0248ef826a28c50ae21992
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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