1-Methyl-4-(3-nitro-4-pyridyl)piperazine → Piperazine, 1-(3-amino-4-pyridyl)-4-methyl-

HRID 524858Notes

Reaction equation

HRID 524858 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 867209151-Methyl-4-(3-nitro-4-pyridyl)piperazine

Product 1

HCID 203473Piperazine, 1-(3-amino-4-pyridyl)-4-methyl-Yield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-methyl-4-(3-nitro-4-pyridyl)piperazine 14 (2.56 g, 11.52 mmol) in methanol (200 mL) was treated with palladium on carbon (10% wt % Degussa) (300 mg) and hydrogenated under balloon pressure at RT for 3 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 4-(4-methylpiperazin-1-yl)pyridin-3-amine 15 as a colourless solid (2.124 g, 11.05 mmol, 95.89%). MS (ES+) 193.1.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a274879ee2c240a49f1b5bf42142de87
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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