Water → 1-Acetyl-4-(2',4'-difluorobenzoyl)piperidine

HRID 370881Notes

Reaction equation

HRID 370881 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1.[C:13]([N:16]1[CH2:24][CH2:23][CH:19]([C:20](Cl)=[O:21])[CH2:18][CH2:17]1)(=[O:15])[CH3:14].O>CCCCC>[C:13]([N:16]1[CH2:17][CH2:18][CH:19]([C:20](=[O:21])[C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][C:8]=2[F:12])[CH2:23][CH2:24]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 97411,3-DifluorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27407071-Acetyl-4-(2',4'-difluorobenzoyl)piperidineYield 65.9%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a slurry of 6.6 g of aluminum chloride and 20 ml of 1,3-difluorobenzene was added, with stirring at ambient temperature, 5.0 g of N-acetylisonipecotyl chloride. The reaction mixture was heated under reflux for 11/2 hrs and then poured onto 100 ml of ice and water. The mixture was extracted with chloroform. The chloroform fractions were combined, washed with water and dried over anhydrous magnesium sulfate and filtered. Evaporation of the filtrate gave an oil. Trituration of the oil with pentane gave 4.65 g (65.9%) of product, mp, 100°-102°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 11/2 hrs
  3. extractionThe mixture was extracted with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customEvaporation of the filtrate
  8. customgave an oil

Sources & evidence

ORD record
ord-4d3cd9a2c5f2409dba84decf85b29409
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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