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

HRID 2115880Notes

Reaction equation

HRID 2115880 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-methylpiperazineYield 49.8%

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-methylpiperazine and the residue dissolved in 1M—hydrochloric acid (30 mL). After washing twice with 20 mL portions of DCM the solution was basified with 5 M—sodium hydroxide (10 mL). The product was extracted into DCM (twice with 20 mL), dried over sodium sulphate and evaporated giving 1.50 g yellow oil which solidified on standing

Workup

  1. customevaporated
  2. customto remove all excess N-methylpiperazine
  3. dissolutionthe residue dissolved in 1M—hydrochloric acid (30 mL)
  4. washAfter washing twice with 20 mL portions of DCM the solution
  5. extractionThe product was extracted into DCM (twice with 20 mL),
  6. dry with materialdried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-25b64d254cd74a22a4228c62812bc242
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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