1-Isopropyl-4-(4-nitrobenzyl)piperazine → 4-((4-Isopropylpiperazin-1-yl)methyl)benzenamine

HRID 1189741Notes

Reaction equation

HRID 1189741 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>[Ni].CO>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 8826511-Isopropyl-4-(4-nitrobenzyl)piperazine

Product 1

HCID 282937134-((4-Isopropylpiperazin-1-yl)methyl)benzenamineYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-isopropyl-4-(4-nitro-benzyl)-piperazine (Step 11.2) (5.7 g, 21.65 mmol) and Raney Nickel (2 g) in MeOH (100 mL) was stirred for 6 h at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and concentrated to afford 4.9 g of the title compound as a white solid: ESI-MS: 234.2.

Workup

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

Sources & evidence

ORD record
ord-a2809651b6014fd1bb7a084d3018e6d4
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

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