Potassium Iodide → HCID 12286655, compound

HRID 1580140Notes

Reaction equation

HRID 1580140 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:16][CH:13]([NH:14][CH2:15]2)[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[C:17]([CH2:25][CH2:26][CH2:27][Cl:28])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[O-2].[Al+3].[O-2].[O-2].[Al+3]>C1C=CC=CC=1.O.C1(C)C=CC=CC=1>[ClH:28].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:16][CH:13]([N:14]([CH2:27][CH2:26][CH2:25][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:15]2)[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2535334-ChlorobutyrophenoneHCID 3045729HCID 3045729, compoundHCID 9989226Alumina

Product 1

HCID 12286655HCID 12286655, compoundYield 32.9%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 0.8 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane, 0.74 g of 3-benzoylpropyl chloride, 0.8 g of potassium carbonate, 0.05 g of potassium iodide and 20 ml of toluene is refluxed for 24 hours. After cooling, water is added to the mixture, and the aqueous mixture is extracted with ether. The ether extract is washed with water, dried and then evaporated to remove solvent. The residue thus obtained is dissolved in 2 ml of benzene. The benzene solution is poured onto a column of 50 g of aluminium oxide. Then, the column is eluted with a mixture of 400 ml of benzene and 400 ml of n-hexane, and the effluent is evaporated to remove solvent. Methanolic hydrogen chloride is added to the residue in ether, and the crystalline precipitate is collected by filtration. The precipitate is recrystallized from a mixture of ethanol and ether. 0.485 g of 1-(3-methoxyphenyl)- 6-(3-benzoylpropyl)-6-azabicyclo[3,2,1]octane hydrochloride is obtained. M.p. 167° - 169°C.

Workup

  1. temperatureis refluxed for 24 hours
  2. temperatureAfter cooling
  3. extractionthe aqueous mixture is extracted with ether
  4. extractionThe ether extract
  5. washis washed with water
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue thus obtained
  10. washThen, the column is eluted with a mixture of 400 ml of benzene and 400 ml of n-hexane
  11. customthe effluent is evaporated
  12. customto remove solvent
  13. additionMethanolic hydrogen chloride is added to the residue in ether
  14. filtrationthe crystalline precipitate is collected by filtration
  15. customThe precipitate is recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-35de770c1ba94f029f093c96779fa6ec
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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