Benzene, 1-fluoro-2-methyl-4-nitro- → 1-(2-Methoxy-ethyl)-4-(2-methyl-4-nitro-phenyl)-piperazine

HRID 469833Notes

Reaction equation

HRID 469833 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>CC(N(C)C)=O>[CH3:12][O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH3:11])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 27346381-(2-Methoxyethyl)piperazine

Product 1

HCID 674588251-(2-Methoxy-ethyl)-4-(2-methyl-4-nitro-phenyl)-piperazine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 0.95 g (6.06 mmol) 2-fluoro-5-nitrotoluene and 0.99 g (6.67 mmol) 1-(2-methoxyethyl)piperazine in 10 ml dimethylacetamide is stirred at 120° C. for 20 h. After that the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, EtOAc) to afford the title compound as an oil.

Workup

  1. additionAfter that the reaction mixture is poured on water
  2. extractionextracted 3× with EtOAc
  3. washThe combined organic layers are washed with water and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by chromatography (silicagel, EtOAc)

Sources & evidence

ORD record
ord-365271319e324cc3a360d9131a2f9097
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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