Sodium Chloride → HCID 23144254, compound

HRID 2238714Notes

Reaction equation

HRID 2238714 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].Br[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1.[Cl-].[Na+]>CN(C=O)C>[O:9]=[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][N:3]1[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 23144254HCID 23144254, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% sodium hydride (600 mg, 15.0 mmol) was suspended in DMF (30 mL), 2-piperidone (1.49 g, 15.0 mmol) was added thereto, followed by stirring at room temperature for 30 minutes. A solution of methyl 4-bromomethylbenzoate (2.29 g, 10.0 mmol) in DMF (10 mL) was added to the reaction mixture, followed by stirring at room temperature for 3 hours. The reaction mixture was poured into a saturated aqueous solution of sodium chloride, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate:methanol=9:1) to afford methyl 4-[(2-oxopiperidino)methyl]benzoate (2.47 g 100%).

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-89e55883878e42de8cf3f3f7f4237a6d
Source dataset
uspto-grants-2010_05
Patent number
US07718808B2

Reaction notes

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