Sodium Hydroxide → HCID 68697852, compound

HRID 432783Notes

Reaction equation

HRID 432783 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=1[CH:12]=O.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Cl-].[Na+].O>[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=1[CH:12]=[C:4]1[C:5](=[O:8])[C:6](=[CH:12][C:11]2[C:10]([F:9])=[CH:17][CH:16]=[CH:15][C:14]=2[F:18])[CH2:7][N:2]([CH3:1])[CH2:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 1362842,6-Difluorobenzaldehyde

Product 1

HCID 68697852HCID 68697852, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1.0 g (8.84 mmol) of 1-methylpiperidine-4-one and 2.57 g (18.09 mmol) of 2,6-difluoro benzaldehyde in 90 mL of a 0.25M solution of aqueous NaOH (22.59 mmol) was added 1.16 mL (0.88 mmol) of a 25% w/w aqueous solution of cetyltrimethylammonium chloride. The mixture was allowed to stir vigorously at room temperature for 12 hours, diluted with 100 ml of brine and extracted with three 40 mL portions of methylene chloride. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was slurried in 100 ml of boiling ethyl acetate and the insolubles were removed by rapid suction filtration. The filtrate was concentrated in vacuo and recrystallized from ethyl acetate to provide 3.01 g (94%) of a bright yellow solid.

Workup

  1. extractionextracted with three 40 mL portions of methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customthe insolubles were removed by rapid suction filtration
  5. concentrationThe filtrate was concentrated in vacuo
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3bc4a9ba744844abbd8ca62441192029
Source dataset
uspto-grants-2003_12
Patent number
US06664272B2

Reaction notes

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