1-Methylpiperazine → 1-Methyl-4-(4-methyl-3-nitrophenyl)piperazine

HRID 1907440Notes

Reaction equation

HRID 1907440 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 581716321-Methyl-4-(4-methyl-3-nitrophenyl)piperazineYield 48.3%

Conditions

Temperature
200 °C

Procedure

In a cylindrical quartz tube were placed 4-fluoro-1-methyl-2-nitro-benzene (20.0 g, 129 mmol) and N-methyl-piperazine (26 g, 258 mmol). The reaction was heated for 48 hours at 200° C. until HPLC revealed the disappearance of the starting material. The solvent was removed under reduced pressure and the residue was dissolved in DCM. The solution was washed twice with water and the organic phase was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The final compound (14.65 g, 48% yield) was obtained as a brown oil.

Workup

  1. customIn a cylindrical quartz tube were placed
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. washThe solution was washed twice with water
  5. dry with materialthe organic phase was dried over anhydrous Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a93557995aac4e9bacc2228476afc19f
Source dataset
uspto-grants-2013_12
Patent number
US08598172B2

Reaction notes

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