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

HRID 26693

Reaction equation

HRID 26693 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]([N:15]1[CH2:23][CH2:22][CH:18]([C:19](Cl)=[O:20])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]>>[C:12]([N:15]1[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)[CH2:22][CH2:23]1)(=[O:14])[CH3:13]

Participants

4

Reactant 3

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

Product 1

HCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidineYield 80%

Procedure

A mixture of 93 g. (0.7 mole) of aluminum chloride in 150 ml. of fluorobenzene was stirred while 70 g. (0.37 mole) of 1-acetylisonipecotic acid chloride was added in small portions. After the addition was complete, the mixture was refluxed for one hour. The mixture was poured onto ice and the two layers separated. The aqueous layer was extracted twice with chloroform and the chloroform extracts were added to the organic layer. The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and 73.7 g. (80%) of 1-acetyl-4-(p-fluorobenzoyl)piperidine was obtained as a crystalline residue. Recrystallization from ligroin-isopropyl ether gave a white crystalline product melting at 75°-78° C.

Workup

  1. additionA mixture of 93 g
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for one hour
  4. additionThe mixture was poured onto ice
  5. customthe two layers separated
  6. extractionThe aqueous layer was extracted twice with chloroform
  7. additionthe chloroform extracts were added to the organic layer
  8. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ee895e6a3032440181a2352a3d25ed1a
Source dataset
uspto-grants-1979_04
Patent number
US04151285

Linked notes

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