Water → 6-[2-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-1-methyl-1H-pyrazin-2-one

HRID 914895Notes

Reaction equation

HRID 914895 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[O:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[NH:19][C:18](=[O:20])[CH:17]=[N:16][CH:15]=2)[CH2:8][CH2:7]1.[H-].[Na+].[CH3:27]I.O>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[O:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][C:14]2[N:19]([CH3:27])[C:18](=[O:20])[CH:17]=[N:16][CH:15]=2)[CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 97976346-[2-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-1H-pyrazin-2-one

Product 1

HCID 222484376-[2-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-1-methyl-1H-pyrazin-2-oneYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 330 mg of 6-[2-[4-(2-fluorophenoxymethyl)piperidino]ethyl]-1H-pyrazin-2-one in 3 ml of N,N-dimethylformamide, 44 mg of sodium hydride (70% suspension in oil) was added while stirring, and the stirring was continued for 1 hour at room temperature. Next, 0.068 ml of methyl iodide was added and the mixture was stirred overnight at room temperature. Water 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). Diethyl ether was added and the mixture was filtered to obtain the title compound (116 mg, 34% yield).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. washThe organic layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (solvent: ethyl acetate)
  7. additionDiethyl ether was added
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-2fa00e45a69849a99ff9c77e6a92120a
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

Loading…