Piperazine → 1-(2,6-Difluoro-4-nitrophenyl)piperazine

HRID 77427Notes

Reaction equation

HRID 77427 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[C:12]([F:15])[C:13]=1F>C(#N)C>[F:7][C:8]1[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[C:12]([F:15])[C:13]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 674133721-(2,6-Difluoro-4-nitrophenyl)piperazineYield 96.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of piperazine (24 g, 0.28 mol) and 3,4,5-trifluoronitrobenzene (13 mL, 0.11 mol) in acetonitrile (200 mL) was stirred at 60° C. The progress of reaction was monitored by TLC. On completion, acetonitrile was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL) and resulting solution was washed with water (100 mL), brine (100 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:9 methanol:chloroform) to provide title compound (25.8 g, 92%) as orange solid.

Workup

  1. customThe progress of reaction
  2. customOn completion, acetonitrile was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  4. customresulting solution
  5. washwas washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-a9d4a88fdc2640788d0e6650632f5109
Source dataset
uspto-grants-2014_09
Patent number
US08841306B2

Reaction notes

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