1-Ethyl-4-(5-nitropyridin-2-yl)piperazine → 6-(4-Ethylpiperazin-1-yl)pyridin-3-amine

HRID 409697Notes

Reaction equation

HRID 409697 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2]>CO.[Ni]>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[N:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 1

HCID 28489801-Ethyl-4-(5-nitropyridin-2-yl)piperazine

Product 1

HCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-ethyl-4-(5-nitro-pyridin-2-yl)-piperazine (1.4 g) and Raney-Nickel (140 mg) in MeOH (30 mL) is stirred for 10 h at RT, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford the title compound as a purple oil: ESI-MS: 207.1 [MH]+; TLC: Rf=0.26 (DCM/MeOH/NH3aq, 94:5:1).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-98c638f7bc3844969d378e418c8060d6
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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