1-Methylpiperazine → 1-(2-Fluoro-4-nitrophenyl)-4-methylpiperazine

HRID 2117622Notes

Reaction equation

HRID 2117622 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1F>>[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 27830541-(2-Fluoro-4-nitrophenyl)-4-methylpiperazine

Conditions

Temperature
100 °C

Procedure

N-Methylpiperazine (30 mL, 27.1 g, 0.268 mol) was cooled in ice/water while adding 3,4-difluoronitrobenzene (2.0 g, 0.0126 mol) with stirring. The mixture was then heated at 100° C. overnight, evaporated to remove all excess N-methyl-piperazine and the residue dissolved in 1M hydrochloric acid (30 mL). After washing twice with 20 mL portions of dichloromethane the solution was basified with 5M sodium hydroxide (10 mL). The product was extracted into dichloro-methane (twice with 20 mL), dried over sodium sulphate and evaporated giving a yellow oil which solidified on standing. 1H NMR (CDCl3) 8.00 (m, 1H) 7.91 (m, 1H) 6.92 (m, 1H) 3.33 (m, 4H) 2.63 (m, 4H) 2.39 (s, 3H).

Workup

  1. customevaporated
  2. customto remove all excess N-methyl-piperazine
  3. dissolutionthe residue dissolved in 1M hydrochloric acid (30 mL)
  4. washAfter washing twice with 20 mL portions of dichloromethane the solution
  5. extractionThe product was extracted into dichloro-methane (twice with 20 mL),
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customgiving a yellow oil which

Sources & evidence

ORD record
ord-58f64c915dc74d96ab696040c0243a0d
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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