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

HRID 880492Notes

Reaction equation

HRID 880492 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 98.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(4,6-dimethyl-2-pyridyl)-4-(4-nitrophenyl)piperazine (49 g, 157 mmol) in methanol was hydrogenated over Raney Nickel (15 g) at 90 psi pressure for 36 h. The mixture was filtered through Celite and the filtrate was concentrated in vacuo giving a crude product which was washed with petroleum ether (100 mL) to afford 4-[4-(4,6-dimethyl-2-pyridyl)piperazin-1-yl]aniline (43.5 g, 98%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customgiving a crude product which
  4. washwas washed with petroleum ether (100 mL)

Sources & evidence

ORD record
ord-29668b47748745f2b8b8c5a2a8e94f4c
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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