Iodine → HCID 19983093, compound

HRID 1460239Notes

Reaction equation

HRID 1460239 reaction equation
[P].II.CS(O)(=O)=[O:6].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:12][CH:11]=1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>C(O)(=O)C.CO.CCOCC.O>[OH2:6].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)[CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:24][CH:25]=1

Participants

10

Reactant 5

HCID 807IodineHCID 6395Methanesulfonic AcidHCID 444972Fumaric AcidHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 5462309Phosphorus

Product 1

HCID 19983093HCID 19983093, compoundYield 32%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 30.6 g (0.99 mole) of phosphorous and 15.1 g (0.059 mole) of iodine in 90 ml of glacial acetic acid was stirred for 20 min at room temperature. A mixture of 6 ml of water, 70 ml of methanesulfonic acid, 56.19 g (0.197 mole) of 4-[bis(4-fluorophenyl)methylene]piperidine and 110 ml of glacial acetic acid was added, and the mixture was heated at reflux for 7 hr. The solvent was removed in vacuo, and the resulting viscous liquid was poured over ice. The icy mixture was made basic with 50% sodium hydroxide, and the basic suspension was extracted with methylene chloride. The methylene chloride solution was extracted with an aqueous solution of sodium thiosulfate and was dried over anhydrous sodium sulfate, and the solution was filtered through Celite®. The solvent was removed in vacuo to give a gum. The gum was dissolved in 400 ml of hot methanol, and 4.25 g of an unknown tan solid was collected from the warm solution. Fumaric acid (22 g, 0.19 mole) was added to the methanolic solution followed by the addition of ether. A white precipitate was collected to give 22.55 g (32%) of crystalline solid, mp 208°-209° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 7 hr
  4. customThe solvent was removed in vacuo
  5. additionthe resulting viscous liquid was poured over ice
  6. extractionthe basic suspension was extracted with methylene chloride
  7. extractionThe methylene chloride solution was extracted with an aqueous solution of sodium thiosulfate
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. filtrationthe solution was filtered through Celite®
  10. customThe solvent was removed in vacuo
  11. customto give a gum
  12. custom4.25 g of an unknown tan solid was collected from the warm solution
  13. customA white precipitate was collected

Sources & evidence

ORD record
ord-c7146135a93c45878e338ad5b94803a9
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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