Piperazine → 1-(3-Methyl-2-pyridinyl)piperazine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe reaction heated
- temperatureto reflux for 3 days
- temperatureThe mixture was cooled
- customthe solvent removed under reduced pressure
- customThe residue was partitioned between water and ethyl acetate
- dry with materialThe organic phase was dried (sodium sulfate)
- concentrationconcentrated
- 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
Reaction notes
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