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

HRID 1925385Notes

Reaction equation

HRID 1925385 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-8b07e03ab33644f2af540666dffd68aa
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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