Piperazine → 1-(3-Nitropyridin-2-yl)piperazine

HRID 325611

Reaction equation

HRID 325611 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(#N)C>[N+:8]([C:7]1[C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 37788341-(3-Nitropyridin-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chloro-3-nitropyridine (4.76 g, 30 mmol) and piperazine (5.9, 69 mmol) in acetonitrile, (75 mL), was stirred at reflux for 5 h. After concentrating under reduced pressure, the residue was partitioned between ethyl acetate and 10% NaOH. The ethyl acetate extract was washed with water, dried (Na2SO4), filtered and concentrated. Flash chromatography over Al2O3 and elution with 2% MeOH-98% CHCl3 afforded the title compound, m.p. 82°-87° C. An analytical sample, m.p. 83.5°-86.5° C., was obtained upon recrystallization from CHCl3 -hexane.

Workup

  1. temperatureat reflux for 5 h
  2. concentrationAfter concentrating under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 10% NaOH
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatography over Al2O3 and elution with 2% MeOH-98% CHCl3

Sources & evidence

ORD record
ord-354e584d27204713935bafa4bda00ee9
Source dataset
uspto-grants-1984_04
Patent number
US04442103

Linked notes

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