1-(4,6-Dimethyl-pyridin-2-yl)-4-(4-nitro-phenyl)-piperazine → 4-[4-(4,6-Dimethyl-2-pyridyl)piperazin-1-yl]aniline

HRID 37875Notes

Reaction equation

HRID 37875 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[CH:3]=1>CO.[Ni]>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[CH:3]=1

Participants

4

Reactant 1

HCID 668512921-(4,6-Dimethyl-pyridin-2-yl)-4-(4-nitro-phenyl)-piperazine

Product 1

HCID 668513514-[4-(4,6-Dimethyl-2-pyridyl)piperazin-1-yl]anilineYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A slurry of 1-(4,6-dimethyl-pyridin-2-yl)-4-(4-nitro-phenyl)-piperazine (27 g, 86.5 mmol) in methanol (1 L) was hydrogenated over Raney nickel (8 g) at 70-75 psi and room temperature in a Parr hydrogenation apparatus until no starting material was observed on TLC. The mixture was filtered through Celite and the filtrate concentrated in vacuo to afford 4-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-phenyl amine (22.2 g, 91%) as a solid which needed no further purification and was used as such in the next step.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8b483365a965465c90414b316bf59e63
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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