Ethyl Acetate → 3-[1-[4-[2-(2-Fluorophenyl)acetyl]piperidino]ethyl]-1H-pyrazin-2-one

HRID 606256Notes

Reaction equation

HRID 606256 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

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 222484241-[1-[1-(3-Methoxy-2-pyrazinyl)ethyl]piperidin-4-yl]-2-(2-fluorophenyl)ethanone

Product 1

HCID 101721963-[1-[4-[2-(2-Fluorophenyl)acetyl]piperidino]ethyl]-1H-pyrazin-2-oneYield 53.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

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

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 9 hours
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (solvent: ethyl acetate/methanol), diethyl ether
  8. additionwas added
  9. filtrationthe precipitate was filtered out

Sources & evidence

ORD record
ord-26c0d0d1bdbf4214894c71f8ed2269ec
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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