Hydrochloric Acid → (2-Fluorophenyl)(piperidin-4-yl)methanone--hydrogen chloride (1/1)

HRID 867019Notes

Reaction equation

HRID 867019 reaction equation
O(C([N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:12][CH2:11]1)=O)C1C=CC=CC=1.[OH-].[K+].[ClH:27]>C(O)C.O>[ClH:27].[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([CH:13]1[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]1)=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13180319HCID 13180319, compound

Product 1

HCID 13180313(2-Fluorophenyl)(piperidin-4-yl)methanone--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 40.5 g of 1-phenoxycarbonyl-4-(2-fluorobenzoyl)piperidine in 500 ml of ethanol and 500 ml of an aqueous 30% potassium hydroxide solution is stirred at a temperature slightly below reflux for 16 hours, allowed to cool to ambient temperature, diluted with water, and the ethanol is partially removed under reduced pressure. The resulting aqueous suspension is extracted with ether, the combined ether extracts are extracted with 1N hydrogen chloride and the aqueous acid solution is basified with an aqueous sodium hydroxide solution. The basic solution is extracted with ether, the combined ether extracts are dried and the ether is removed under reduced pressure leaving a dark oil. The oil is dissolved in a minimum amount of ethanol and ethereal-hydrogen chloride is added dropwise to effect a precipitate. The precipitate is collected by filtration, dried and recrystallized twice from an ethanol-ether mixture to give a white solid, mp 185°-187° C., 4-(2-fluorobenzoyl)piperidine hydrochloride.

Workup

  1. temperaturebelow reflux for 16 hours
  2. customthe ethanol is partially removed under reduced pressure
  3. extractionThe resulting aqueous suspension is extracted with ether
  4. extractionthe combined ether extracts are extracted with 1N hydrogen chloride
  5. extractionThe basic solution is extracted with ether
  6. dry with materialthe combined ether extracts are dried
  7. customthe ether is removed under reduced pressure
  8. customleaving a dark oil
  9. filtrationThe precipitate is collected by filtration
  10. customdried
  11. customrecrystallized twice from an ethanol-ether mixture

Sources & evidence

ORD record
ord-65f06ed50f84414b8e821e9b53b4e77b
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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