1-Methyl-4-[2-(3-methyl-4-nitrophenoxy)ethyl]piperazine → 2-Methyl-4-[2-(4-methylpiperazinyl)ethoxy]aniline

HRID 402680Notes

Reaction equation

HRID 402680 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([CH3:20])[CH:12]=2)[CH2:4][CH2:3]1>C(O)C.[Pd]>[CH3:20][C:13]1[CH:12]=[C:11]([O:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:16]=[CH:15][C:14]=1[NH2:17]

Participants

4

Reactant 1

HCID 8029971-Methyl-4-[2-(3-methyl-4-nitrophenoxy)ethyl]piperazine

Product 1

HCID 392015182-Methyl-4-[2-(4-methylpiperazinyl)ethoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Methyl-4-[2-(3-methyl-4-nitrophenoxy)ethyl]piperazine (0.69 g, 2.5 mmol) was dissolved in ethanol (10 mL) and 10% wt palladium on carbon (0.055 g) was added at ambient temperature. The reaction mixture was agitated under a hydrogen atmosphere at ambient temperature for 4 h. Palladium on carbon was removed by filtration with Celite and the solvent was removed under reduced pressure to afford 2-methyl-4-[2-(4-methylpiperazinyl)ethoxy]aniline as oil (0.60 g, y. 97%).

Workup

  1. customPalladium on carbon was removed by filtration with Celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7721d480015c42808f5cf58def9beb3b
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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