1-Chloro-4-nitrobenzene → HCID 9311031, compound

HRID 880482Notes

Reaction equation

HRID 880482 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>COCCOCCOC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:26]2[CH2:27][CH2:28][N:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=3)[CH2:24][CH2:25]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazine

Product 1

HCID 9311031HCID 9311031, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of 1-chloro-4-nitro-benzene (4.34 g, 27.6 mmol) and anhydrous potassium carbonate (5.08 g, 36.8 mmol) was added to a solution of 1-(2-pyridyl)piperazine (3.0 g, 18.4 mmol) in diglyme (10 mL) and heated at reflux for 24 h. The reaction mixture was cooled to ambient temperature, filtered and the filtrate was concentrated in vacuo. The residue was diluted with chloroform and the organic layer was washed with water (5×40 mL), brine (3×30 mL), dried over anhydrous sodium sulphate and concentrated to yield a crude compound. This was purified by washing with hexane (5×5 mL) and then pentane (2×5 mL) to afford 1-(4-nitrophenyl)-4-(2-pyridyl)piperazine (4.0 g, 77%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was diluted with chloroform
  6. washthe organic layer was washed with water (5×40 mL), brine (3×30 mL)
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated
  9. customto yield a crude compound
  10. customThis was purified
  11. washby washing with hexane (5×5 mL)

Sources & evidence

ORD record
ord-5f59abcf51594e4d9e8638afe5428eb3
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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