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

HRID 1661012Notes

Reaction equation

HRID 1661012 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 124.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-isopropyl-4-(4-nitro-benzyl)-piperazine (5.7 g, 21.65 mmol) and Raney Nickel (2 g) in MeOH (100 mL) is stirred for 6 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated to afford 6.3 g of the title compound as a white solid: ESI-MS: 234.1 [M+H]+; tR=0.95 min (System 1).

Workup

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

Sources & evidence

ORD record
ord-f5e98f18669e4da5aafb80452c166a08
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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