Potassium Hydroxide → HCID 14698744, compound

HRID 476931Notes

Reaction equation

HRID 476931 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[OH:11])[CH2:6][CH2:5]1)(=O)C.[OH-].[K+]>C(O)C.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([CH:7]2[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]2)[OH:11])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 14698741HCID 14698741, compound

Product 1

HCID 14698744HCID 14698744, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 16.3 g (0.05 mole) of 1-acetyl-α-(4-fluorophenyl)-α-phenyl-4-piperidinemethanol and 5.6 g (0.1 mole) of potassium hydroxide in 150 ml of 95% ethanol and 20 ml of water was heated at reflux for 18 hr. The mixture was poured into 1.5 liter of ice water and a solid precipitated. The solid was collected by filtration and dried. The gummy solid was dissolved in ethyl ethyl ether, the solution was filtered, and the filtrate slowly evaporated to 50 ml volume. The resulting solid was collected by filtration and recrystallized from 2-propanol-isopropyl ether to yield 3.5 g (25%) of white solid, m.p. 144.5°-146° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hr
  3. customa solid precipitated
  4. filtrationThe solid was collected by filtration
  5. customdried
  6. dissolutionThe gummy solid was dissolved in ethyl ethyl ether
  7. filtrationthe solution was filtered
  8. customthe filtrate slowly evaporated to 50 ml volume
  9. filtrationThe resulting solid was collected by filtration
  10. customrecrystallized from 2-propanol-isopropyl ether

Sources & evidence

ORD record
ord-9575338ee9664fcfbae6de7d54e1cb2c
Source dataset
uspto-grants-1989_12
Patent number
US04886794

Reaction notes

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