Piperazine → 1-(3-Fluoro-1-oxido-2-pyridinyl)piperazine

HRID 1263223Notes

Reaction equation

HRID 1263223 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:9].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C(O)CCC>[N:10]1([C:2]2[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N+:3]=2[O-:9])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 49131402-Chloro-3-fluoropyridine N-oxide

Product 1

HCID 704816081-(3-Fluoro-1-oxido-2-pyridinyl)piperazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-chloro-3-fluoropyridine N-oxide (400 mg, 3.0 mmol) and piperazine (1.3 g, 15 mmol) in n-butanol, 15 ml, is stirred at reflux for 20 hours. After concentrating under reduced pressure at 55°-60° C., the residue is chromatographed over silica gel and the crude N-oxide eluted with a 50% methanol-methylene chloride solvent mixture. The appropriate eluate is concentrated to an oily residue of the title compound.

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationAfter concentrating under reduced pressure at 55°-60° C.
  3. customthe residue is chromatographed over silica gel
  4. washthe crude N-oxide eluted with a 50% methanol-methylene chloride solvent mixture
  5. concentrationThe appropriate eluate is concentrated to an oily residue of the title compound

Sources & evidence

ORD record
ord-6a3fe72decea4c029480d68a3e741bac
Source dataset
uspto-grants-1984_06
Patent number
US04456604

Reaction notes

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