Potassium Iodide → HCID 21568339, compound

HRID 1579328Notes

Reaction equation

HRID 1579328 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:37])[CH2:33][CH2:34][CH2:35]Cl)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C(=O)(O)[O-].[K+].[I-].[K+]>O.C1(C)C=CC=CC=1>[ClH:21].[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:32](=[O:37])[CH2:33][CH2:34][CH2:35][N:12]2[CH2:13][CH2:14][CH:9]([C:7]([OH:8])([C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:10][CH2:11]2)=[CH:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516893Potassium BicarbonateHCID 27236944'-tert-Butyl-4-chlorobutyrophenoneHCID 12795120HCID 12795120, compound

Product 1

HCID 21568339HCID 21568339, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 11 g (0.035 mole) of α-phenyl-α-(p-chlorophenyl)-4-piperidinemethanol, 12.5 g (0.05 mole) of 4'-tert-butyl-4-chlorobutyrophenone, 10 g of potassium bicarbonate, 0.1 g of potassium iodide, 100 ml of toluene and 10 ml of water is refluxed with stirring for about 93 hours. Upon cooling to room temperature the mixture is filtered and the toluene layer is separated. The aqueous layer is extracted with toluene. The combined organic fractions are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, and filtered. To the filtrate is added an equal volume of ether followed by treatment with ethereal HCl. The resulting precipitate is collected and recrystallized from methanol-butanone to give 4'-tert-butyl-4-[4-[α-hydroxy-α-(p-chlorophenyl)benzyl]-piperidino]butyrophenone hydrochloride, M.P. 238.5°-240°C.

Workup

  1. temperatureis refluxed
  2. filtrationis filtered
  3. customthe toluene layer is separated
  4. extractionThe aqueous layer is extracted with toluene
  5. washThe combined organic fractions are washed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. additionTo the filtrate is added an equal volume of ether
  9. customThe resulting precipitate is collected
  10. customrecrystallized from methanol-butanone

Sources & evidence

ORD record
ord-7308669c48824978b118ea29e628ebca
Source dataset
uspto-grants-1976_01
Patent number
US03931197

Reaction notes

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