Ethyl Acetate → (E)-3-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-1H-pyrazin-2-one
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[C:18]([O:23]C)=[N:19][CH:20]=[CH:21][N:22]=2)[CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)C.S(Cl)(Cl)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[C:18](=[O:23])[NH:19][CH:20]=[CH:21][N:22]=2)[CH2:14][CH2:15]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
After dissolving 296 mg of (E)-3-[4-[2-(2-fluorophenyl)vinyl]piperidino]methyl-2-methoxypyrazine in 5 ml of ethanol, 1 ml of thionyl chloride was added and the mixture was heated to reflux for 9 hours. Aqueous sodium carbonate solution was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and the mixture was filtered to obtain the title compound (180 mg, 63% yield).
Workup
- additionwas added
- temperaturethe mixture was heated
- temperatureto reflux for 9 hours
- washThe organic layer was washed with water and saturated brine in that order
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- additionEthyl acetate was added to the residue
- filtrationthe mixture was filtered
Sources & evidence
- ORD record
- ord-244edb0f38464807816be31398178802
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915274B2
Reaction notes
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