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

HRID 914892Notes

Reaction equation

HRID 914892 reaction equation
C([O:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[CH2:16][CH2:15]2)[N:7]=1)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C(OCC)(=O)C.Cl.C(OCC)(=O)C>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[O:21][CH2:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][C:8]2[NH:7][C:6](=[O:5])[CH:11]=[N:10][CH:9]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 222480162-Tert-butoxy 6-[2-[4-(2-fluorophenoxymethyl)piperidino]ethyl]pyrazine

Product 1

HCID 97976346-[2-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-1H-pyrazin-2-oneYield 79.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

After dissolving 167 mg of 2-tert-butoxy 6-[2-[4-(2-fluorophenoxymethyl)piperidino]ethyl]pyrazine in 3 ml of ethyl acetate, 3 ml of 4N hydrogen chloride/ethyl acetate was added and the mixture was allowed to stand at room temperature for 30 minutes. Aqueous sodium carbonate solution was added to the reaction solution and extraction was performed with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (113 mg, 79% yield).

Workup

  1. additionwas added
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionDiethyl ether was added to the residue
  6. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-fb047102c64a4ff1b7679e7ecb48df65
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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