Potassium Iodide → HCID 15872105, compound

HRID 617374Notes

Reaction equation

HRID 617374 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:21])[CH:9]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.C1(C)C=CC(S(O[CH2:32][CH2:33]/[CH:34]=[C:35](\[C:37]([F:40])([F:39])[F:38])/[CH3:36])(=O)=O)=CC=1.C(=O)([O-])[O-:43].[K+].[K+].[I-].[K+]>CN(C)C=O.C(OCC)C>[F:38][C:37]([F:40])([F:39])/[C:35](/[CH3:36])=[CH:34]\[CH2:33][CH2:32][N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:21])[C:9]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)([OH:43])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19349103HCID 19349103, compoundHCID 21851766HCID 21851766, compound

Product 1

HCID 15872105HCID 15872105, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 77 mg of N-(piperidin-4-yl)-2-cyclopentyl-2-phenylacetamide in 3 ml of N,N-dimethylformamide, 74 mg of (3Z)-4-trifluoromethyl-3-pentenyl p-toluenesulfonate, 102 mg of potassium carbonate and 43 mg of potassium iodide were added by the order stated, followed by 3 hours' heating under reflux. The reaction liquid was diluted with diethyl ether, washed with water and saturated saline solution by the order stated, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was purified by preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck) chloroform/methanol=9/1) to provide 27 mg of the title compound as an oily substance.

Workup

  1. temperature' heating
  2. temperatureunder reflux
  3. customThe reaction liquid
  4. washwashed with water and saturated saline solution by the order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationDistilling the solvent off under reduced pressure
  7. customthe residue was purified by preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck) chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-bd10a0330b4b4a8c8d2f236012d2d3dd
Source dataset
uspto-grants-1999_09
Patent number
US05948792

Reaction notes

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