Piperazine → 1-(3-Methyl-2-pyridinyl)piperazine

HRID 490203

Reaction equation

HRID 490203 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>C(O)CCC>[CH3:8][C:7]1[C:2]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 2208322-Bromo-3-methylpyridine

Product 1

HCID 27600571-(3-Methyl-2-pyridinyl)piperazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a slurry of 2-bromo-3-methylpyridine (3.30 mL, 29.6 mmol) in n-butanol was added piperazine (25.0 g, 290 mmol) and the reaction heated to reflux for 3 days. The mixture was cooled and the solvent removed under reduced pressure. The residue was partitioned between water and ethyl acetate. The organic phase was dried (sodium sulfate) and concentrated. The residue was purified by flash column chromatography on silica gel (elution with 15% methanol:dichloromethane) to provide the title compound as a yellow oil.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 3 days
  3. temperatureThe mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. customThe residue was partitioned between water and ethyl acetate
  6. dry with materialThe organic phase was dried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel (elution with 15% methanol:dichloromethane)

Sources & evidence

ORD record
ord-574248bc234740a2bbf0875f2d8c86bc
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Linked notes

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