Potassium Iodide → HCID 21528587, compound

HRID 1658668Notes

Reaction equation

HRID 1658668 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:32])[CH2:28][CH2:29][CH2:30][Cl:31])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(OCC)(=O)C.O.C(C(C)=O)C(C)C>[ClH:31].[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH2:30][CH2:29][CH2:28][C:27]([C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=3)=[O:32])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 882784-Benzhydrylpiperidine

Product 1

HCID 21528587HCID 21528587, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
77 °C

Procedure

A mixture of 125.5 g (0.5 mole) of 4-diphenylmethyl-piperidine, 110 g (0.55 mole) of 4'-fluoro-4-chlorobutyrophenone, 110 g (0.8 mole) of potassium carbonate, a small amount of potassium iodide and 600 ml of methyl isobutyl ketone was refluxed and stirred for 21/2 days, then filtered. The filtrate was concentrated under reduced pressure. The remaining residue was dissolved in ether and treated with ethereal HCl. A gummy residue formed which was dissolved in ethyl acetate with a small amount of water and heated on a steam bath to a vapor temperature of 77°C then cooled. The resulting precipitate was washed with ether and recrystallized from ethyl acetate, toluene and isopropyl alcohol to give the desired product, M.P. 194°-195.5°C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionThe remaining residue was dissolved in ether
  4. additiontreated with ethereal HCl
  5. customA gummy residue formed which
  6. temperaturethen cooled
  7. washThe resulting precipitate was washed with ether
  8. customrecrystallized from ethyl acetate, toluene and isopropyl alcohol

Sources & evidence

ORD record
ord-72021535b106455d942a340132117f6d
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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