Hydrochloric Acid → p-Fluorophenyl 4-piperidyl ketone hydrochloride

HRID 867000Notes

Reaction equation

HRID 867000 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=O)C.[ClH:19]>>[ClH:19].[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([CH:7]2[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]2)=[O:18])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidine

Product 1

HCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Procedure

A solution of 70.6 of 1-acetyl-4-(4-fluorobenzoyl)piperidine in 200 ml of 6N HCl is refluxed for 2 hours. The cooled solution is extracted twice with ether, the aqueous solution basified with sodium hydroxide and then extracted with benzene. The benzene extracts are dried, filtered and the filtrate is concentrated under reduced pressure. The residual oil is dissolved in ether and HCl gas is bubbled into the solution with stirring. The salt is collected by filtration, washed with ether and dried. The salt is recrystallized from isopropanol to give the solid product of 4-(4-fluorobenzoyl)piperidine hydrochloride, mp 222°-224° C.

Workup

  1. extractionThe cooled solution is extracted twice with ether
  2. extractionextracted with benzene
  3. dry with materialThe benzene extracts are dried
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. dissolutionThe residual oil is dissolved in ether
  7. customHCl gas is bubbled into the solution
  8. filtrationThe salt is collected by filtration
  9. washwashed with ether
  10. customdried
  11. customThe salt is recrystallized from isopropanol

Sources & evidence

ORD record
ord-a02031020bc64b1f8543803e0d582b1d
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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