1-Methyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazine → 6-((4-Methylpiperazin-1-yl)methyl)pyridin-3-amine

HRID 1189757Notes

Reaction equation

HRID 1189757 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][N:10]=2)[CH2:4][CH2:3]1>[Ni].CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 669146521-Methyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazine

Product 1

HCID 669146036-((4-Methylpiperazin-1-yl)methyl)pyridin-3-amineYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-methyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazine (Step 39.2) (0.529 g, 2.24 mmol) and Raney nickel (0.1 g) in MeOH (10 mL) was stirred for 1 h at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and concentrated to afford 0.448 g of the title compound as an off-white solid: ESI-MS: 207.2 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4aabc9602e414c69be8f2ad0a3a2dada
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

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