Fluorobenzene → 1-Acetyl-4-(4-fluorobenzoyl)piperidine

HRID 866999Notes

Reaction equation

HRID 866999 reaction equation
[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](Cl)=[O:9])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](=[O:9])[C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidine

Procedure

70 g of 1-acetylisonipecotoyl chloride are slowly added to a stirring mixture of 93.0 g of aluminum chloride in 150 ml of fluorobenzene. After total addition, the mixture is refluxed for one hour. The mixture is poured onto ice and the two resulting layers separate. The aqueous layer is extracted twice with chloroform and the extracts are added to the fluorobenzene which separated previously. The organic solution is dried and concentrated under reduced pressure leaving a crystalline white solid. The solid is recrystallized from a ligroindiisopropyl ether mixture, producing 1-acetyl-4-(4-fluorobenzoyl)piperidine.

Workup

  1. additionAfter total addition
  2. temperaturethe mixture is refluxed for one hour
  3. additionThe mixture is poured onto ice
  4. customthe two resulting layers separate
  5. extractionThe aqueous layer is extracted twice with chloroform
  6. additionthe extracts are added to the fluorobenzene which
  7. customseparated previously
  8. customThe organic solution is dried
  9. concentrationconcentrated under reduced pressure
  10. customleaving a crystalline white solid
  11. customThe solid is recrystallized from a ligroindiisopropyl ether mixture

Sources & evidence

ORD record
ord-6534c7bbada24589abe23e252eacc832
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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