Potassium Hydroxide → HCID 14698744, compound

HRID 1709854Notes

Reaction equation

HRID 1709854 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 liters of ice-water and a solid precipitated. The gummy solid was collected by filtration and dried. The solid was dissolved in ethyl ether, filtered, and the filtrate slowly evaporated to 50 ml. The resulting solid was collected by filtration and recrystallized from 2-propanolisopropyl ether to yield 3.5 g (25%) of title compound as a white solid, m.p. 144.5°-146° C.

Workup

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

Sources & evidence

ORD record
ord-e4b7a910e8c743c986c351b76e701bb4
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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