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

HRID 652128Notes

Reaction equation

HRID 652128 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]>O.C(O)C>[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)Yield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 40.5 g of 1-phenoxycarbonyl-4-(2-fluorobenzoyl)piperidine, 500 ml of ethanol and 500 ml of 30% of potassium hydroxide solution was stirred at a temperature slightly below reflux overnight. The reaction mixture was cooled to room temperature, diluted with 250 ml of water, and the ethanol partially removed under reduced pressure. The aqueous suspension was extracted with ether (2×150 ml) and the ether fraction subsequently extracted with 1N hydrochloric acid (2×200 ml). The aqueous solution was basified with 25% sodium hydroxide solution, extracted with ether (2×150 ml) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give an oil. The oil was dissolved in a minimum amount of ethanol and a solution of ethereal hydrogen chloride was added dropwise until a precipitate formed. The solid was collected and dried to give 9.7 g (40%) of product. Recrystallization twice from ethanol-ether gave the analytical sample, mp 185°-187° C.

Workup

  1. temperaturebelow reflux overnight
  2. customthe ethanol partially removed under reduced pressure
  3. extractionThe aqueous suspension was extracted with ether (2×150 ml)
  4. extractionthe ether fraction subsequently extracted with 1N hydrochloric acid (2×200 ml)
  5. extractionextracted with ether (2×150 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customto give an oil
  9. customformed
  10. customThe solid was collected
  11. customdried

Sources & evidence

ORD record
ord-a85f8183f1ed4c37b5cf5d441d36b225
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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