HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethyl Acetate → (E)-3-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-1H-pyrazin-2-one

HRID 606227
Notes
Print preview

Reaction equation

HRID 606227 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]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 22248227(E)-3-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-2-methoxypyrazine

Product 1

HCID 22247936(E)-3-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-1H-pyrazin-2-oneYield 63.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 24386
Thionyl Chloride
Solvent

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

  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. additionEthyl acetate was added to the residue
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-244edb0f38464807816be31398178802
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915274B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes