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

HRID 1709860Notes

Reaction equation

HRID 1709860 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](Cl)=[O:13])[CH2:10][CH2:9]1)(=[O:7])[CH3:6].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:5]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](=[O:13])[C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

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 of (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 1 hr. The mixture was poured onto ice and the 2 resulting layers were separated. The aqueous layer was extracted twice with chloroform and the chloroform extracts were added to the fluorobenzene which was separated previously. The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and 73.7 g (80% yield) 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. additionwas added in small portions
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 1 hr
  4. additionThe mixture was poured onto ice
  5. customthe 2 resulting layers were separated
  6. extractionThe aqueous layer was extracted twice with chloroform
  7. additionthe chloroform extracts were added to the fluorobenzene which
  8. customwas separated previously
  9. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6318ce07033c4e3faf2d5fb5c990841d
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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