Ethyl Acetate → 3-[1-[4-[2-(2-Fluorophenyl)acetyl]piperidino]ethyl]-1H-pyrazin-2-one
Reaction equation
C[O:2][C:3]1[C:4]([CH:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17](=[O:26])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[CH2:13][CH2:12]2)[CH3:10])=[N:5][CH:6]=[CH:7][N:8]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C.Cl.C(OCC)(=O)C>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][C:17]([CH:14]1[CH2:13][CH2:12][N:11]([CH:9]([C:4]2[C:3](=[O:2])[NH:8][CH:7]=[CH:6][N:5]=2)[CH3:10])[CH2:16][CH2:15]1)=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
After dissolving 118 mg of 1-[1-[1-(3-methoxy-2-pyrazinyl)ethyl]piperidin-4-yl]-2-(2-fluorophenyl)ethanone in 2 ml of ethanol, 6 ml of 4N hydrogen chloride/ethyl acetate was added and the mixture was heated to reflux for 9 hours. Saturated aqueous sodium bicarbonate 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. The residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol), diethyl ether was added and the precipitate was filtered out to obtain the title compound (61 mg, 38% 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
- customThe residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol), diethyl ether
- additionwas added
- filtrationthe precipitate was filtered out
Sources & evidence
- ORD record
- ord-8c2babbeb6034b4e805aeb4ad6b9e623
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265108B2
Reaction notes
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