Hydrazine → 4-(3,5-Dimethylpiperazin-1-yl)aniline

HRID 2236581Notes

Reaction equation

HRID 2236581 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:3]1.NN>CO.[Ni]>[CH3:8][CH:6]1[NH:7][CH:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5]1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 28296203,5-Dimethyl-1-(4-nitrophenyl)piperazine

Product 1

HCID 176054784-(3,5-Dimethylpiperazin-1-yl)anilineYield 86.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

3,5-Dimethyl-1-(4-nitro-phenyl)-piperazine (1.40 g, 5.90 mmol) is dissolved in 20 ml of methanol with ˜1 g of Raney nickel suspension. Hydrazine (0.576 g, 14.9 mmol) is dissolved in 20 ml of methanol and added dropwise to the reaction mixture over 20 minutes. Mixture is stirred at room temperature for 3 hours. Mixture is filtered through celite and reduced on rotovap to afford the product as a black solid (1.05 g, 67%); 1H NMR (DMSO-d6) δ 0.94 (d, J=6.3 Hz, 6H), 1.93-2.00 (m, 2H), 2.65-2.85 (m, 3H), 3.13-3.20 (m, 2H), 4.45 (bs, 2H), 6.43 (d, J=8.5 Hz, 2H), 6.61 (d, J=8.5 Hz, 2H).

Workup

  1. additionadded dropwise to the reaction mixture over 20 minutes
  2. filtrationMixture is filtered through celite

Sources & evidence

ORD record
ord-ea1c908da0744500b0bc1d3886b3c61a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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