Potassium Iodide → HCID 88630313, compound

HRID 1193698Notes

Reaction equation

HRID 1193698 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[CH:31][C:30]=1[O:38][CH3:39].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.C(Cl)(Cl)Cl.CO.C(OCC)(=O)C.C(OCC)(=O)C>[OH2:28].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[CH:31][C:30]=3[O:38][CH3:39])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1.[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[CH:31][C:30]=3[O:38][CH3:39])[CH2:11][CH2:10]2)[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 144071771-[4-[(5-Chloropentyl)oxy]-3-methoxyphenyl]ethanone

Product 1

HCID 88630313HCID 88630313, compoundYield 36.3%

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 6.03 g (0.021 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine, 5.69 g (0.021 mole) of 1-[4-(5-chloropentoxy)-3-methoxyphenyl]ethanone, and potassium carbonate (5.53 g, 0.04 mole) was heated overnight at gentle reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The reaction mixture was cooled at room temperature, filtered, and striped to dryness. The residue obtained was dissolved in chloroform and extracted several times with water. The chloroform layer was dried (sodium sulfate), filtered, and solvent removed to give a brown oil. This oil was subjected to flsh chromatography on silica gel using ethyl acetate and 2% methanol-ethyl acetate for elution. Fractions of similar purity were combined and solvent removed. The sample was dried in vacuo at 70° C. overnight after being exposed to the atmosphere for 24 hours. A yield of 2.7 g (24.6%) of brown oil was obtained.

Workup

  1. temperaturewas heated overnight
  2. filtrationfiltered
  3. customThe residue obtained
  4. extractionextracted several times with water
  5. dry with materialThe chloroform layer was dried (sodium sulfate)
  6. filtrationfiltered
  7. customsolvent removed
  8. customto give a brown oil
  9. washfor elution
  10. customsolvent removed
  11. customThe sample was dried in vacuo at 70° C. overnight

Sources & evidence

ORD record
ord-7b70d4b996654db1919a363e74182747
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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