1-Methylpiperazine → 2-Methyl-5-[2-(4-methylpiperazin-1-yl)ethyl]pyridin-3-amine

HRID 1892212Notes

Reaction equation

HRID 1892212 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-])=O)[C:6]([CH3:9])=[N:7][CH:8]=1)#[CH:2].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CCO.[OH-].[OH-].[Pd+2]>[CH3:9][C:6]1[C:5]([NH2:10])=[CH:4][C:3]([CH2:1][CH2:2][N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 58476611HCID 58476611, compound

Product 1

HCID 584766652-Methyl-5-[2-(4-methylpiperazin-1-yl)ethyl]pyridin-3-amineYield 77%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-ethynyl-2-methyl-3-nitropyridine (600 mg, 3.70 mmol) in EtOH (10 mL) was added 1-methyl-piperazine (1.64 mL, 14.8 mmol). The reaction mixture was allowed to stir at reflux overnight. The reaction mixture was allowed to cool to rt and palladium hydroxide on carbon (0.060 g) was added to the solution. The reaction mixture was purged with hydrogen and then allowed to stir under an atmosphere of H2 at rt overnight. The reaction mixture was filtered through celite and the filatrate was concentrated. The residue was purified by column chromatography to give 2-methyl-5-[2-(4-methylpiperazin-1-yl)ethyl]pyridin-3-amine (0.664 g, 77%).

Workup

  1. temperatureat reflux overnight
  2. customThe reaction mixture was purged with hydrogen
  3. stirringto stir under an atmosphere of H2 at rt overnight
  4. filtrationThe reaction mixture was filtered through celite
  5. concentrationthe filatrate was concentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-de197839c16146daa81651c60a092528
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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