Potassium Hydroxide → HCID 14698744, compound

HRID 345466Notes

Reaction equation

HRID 345466 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 h. The mixture was poured into 1.5 L of ice-water and a solid precipitated. The solid was collected by filtration and dried. The gummy 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-propanol/isopropyl ether to yield 3.5 g (25%) of white solid, mp 144.5°-146° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customa solid precipitated
  4. filtrationThe solid was collected by filtration
  5. customdried
  6. dissolutionThe gummy 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-propanol/isopropyl ether

Sources & evidence

ORD record
ord-9a3ba8f003a54039a19a0ce70bd0fe32
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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