Potassium Iodide → HCID 86745267, compound

HRID 1460256Notes

Reaction equation

HRID 1460256 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.C(OC(=O)C(=O)[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37]Cl)=[C:30]([O:39][CH3:40])[CH:29]=1)C.[C:43](=[O:46])([O-])[O-:44].[Na+].[Na+].[I-].[K+].[C:51](=O)(O)[O-:52].[Na+].[Cl-].[Na+]>CN(C)C=O.O.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:37][CH2:36][CH2:35][O:34][C:31]3[C:30]([O:39][CH3:40])=[CH:29][CH:28]=[CH:33][C:32]=3[C:51](=[O:52])[C:43]([OH:44])=[O:46])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 15020374HCID 15020374, compound

Product 1

HCID 86745267HCID 86745267, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.02 mole of [α,α-bis(4-fluorophenyl)]-4-piperidinemethanol, 0.02 mole of 4-(3-chloropropyloxy)-3-methoxy-α-oxobenzeneacetic acid ethyl ester, 0.06 mole of anhydrous sodium carbonate and 0.4 g of potassium iodide in 150 ml of dimethylformamide was heated on a steambath overnight. The mixture was poured into 1.5 liters of ice-water, and the ethyl ester of the title compound precipitated. The liquid was decanted, and the gum was dissolved in 100 ml of ethanol. A solution of 0.04 mole of sodium bicarbonate in 20 ml of water was added, and the mixture was heated at reflux overnight and then poured into a solution of 1 liter of water and 5 ml of acetic acid. Sodium chloride was added, and a solid precipitated. The solid was collected by filtration and dried to give the title compound.

Workup

  1. temperaturewas heated on a steambath overnight
  2. customthe ethyl ester of the title compound precipitated
  3. customThe liquid was decanted
  4. dissolutionthe gum was dissolved in 100 ml of ethanol
  5. temperaturethe mixture was heated
  6. temperatureat reflux overnight
  7. customa solid precipitated
  8. filtrationThe solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-fd2f37dd29be49cb9b48cbcbeec76824
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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