p-Fluoronitrobenzene → 3,5-Dimethyl-1-(4-nitrophenyl)piperazine

HRID 2236580Notes

Reaction equation

HRID 2236580 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][CH:12]1[CH2:17][NH:16][CH2:15][CH:14]([CH3:18])[NH:13]1>C(#N)C>[CH3:11][CH:12]1[NH:13][CH:14]([CH3:18])[CH2:15][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 660562,6-Dimethylpiperazine

Product 1

HCID 28296203,5-Dimethyl-1-(4-nitrophenyl)piperazineYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

1-Fluoro-4-nitro-benzene (1.00 g, 8.75 mmol) and 2,6-dimethyl-piperazine (1.20 g, 10.5 mmol) are dissolved in 100 ml of acetonitrile forming a yellow homogeneous mixture. Mixture is heated at 90° C. overnight. Mixture is reduced on rotovap to afford the product as an orange solid (1.40 g, 65%); 1H NMR (DMSO-d6) δ 1.00 (d, J=6.3 Hz, 6H), 2.37-2.80 (m, 5H), 3.87 (dd, J=2.1, 12.4 Hz, 2H), 7.00 (d, J=9.5 Hz, 2H), 8.00 (d, J=9.5 Hz, 2H).

Sources & evidence

ORD record
ord-1307e038e50a42fc89b680f76c2d3ffe
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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