Piperazine → 1-(4-Nitro-2-pyridinyl)piperazine

HRID 1382225Notes

Reaction equation

HRID 1382225 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>N1C=CC=CC=1>[N+:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:7]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 224187101-(4-Nitro-2-pyridinyl)piperazineYield 18.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-chloro-4-nitropyridine (4.89 g), and piperazine (7.90 g) in pyridine (90 ml) was heated under reflux for 5 hours and then evaporated. The residue was dissolved in water and the solution was basified with sodium bicarbonate (to pH 8-9) and then continuously extracted with dichloromethane. The extract was dried (Na2SO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with dichloromethane/methanol/concentrated aqueous ammonia (98:2:1) first gave a solid that was crystallised from ethyl acetate/hexane to give 1-[4-nitro-2-pyridinyl]piperazine (1.21 g), m.p. 92°-93° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in water
  4. extractioncontinuously extracted with dichloromethane
  5. dry with materialThe extract was dried (Na2SO4)
  6. customevaporated
  7. customto give an oil which
  8. customwas chromatographed on silica gel
  9. washElution with dichloromethane/methanol/concentrated aqueous ammonia (98:2:1)
  10. customfirst gave a solid
  11. customthat was crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-59c2ffe96dcb48e5ae1ceb432aee90eb
Source dataset
uspto-grants-1989_02
Patent number
US04806536

Reaction notes

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