Potassium Iodide → HCID 23036309, compound

HRID 1709921Notes

Reaction equation

HRID 1709921 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:11]2[CH2:15][CH2:14][NH:13][CH2:12]2)[C:9]#[N:10])=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][C:29]=1[O:37][CH3:38].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.C(Cl)(Cl)Cl.CO.C(OCC)(=O)C>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([O:27][CH2:26][CH2:25][CH2:24][N:13]2[CH2:14][CH2:15][CH:11]([C:8]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]#[N:10])[CH2:12]2)=[C:29]([O:37][CH3:38])[CH:30]=1)(=[O:36])[CH3:35]

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 15020357HCID 15020357, compound

Product 1

HCID 23036309HCID 23036309, compoundYield 67.4%

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of α,α-bis(4-fluorophenyl)-3-pyrrolidineacetonitrile (5.13 g, 0.0172 mole), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4.17 g, 0.0172 mole), and potassium carbonate (5.53 g, 0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The butanol was removed by rotary evaporation. The residue obtained was dissolved in chloroform and extracted several times with water. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed in vacuo to give a dark brown oil. The oil was subjected to flash chromatography on silica gel using ethyl acetate and 25% methanol-75% ethyl acetate for elution. Fractions of similar purity were combined and solvents removed. A dark brown oil was obtained and dried in vacuo 2 days at 80° C. to give 5.85 g (57.5% yield) of the title compound as a dark brown gum.

Workup

  1. temperaturewas heated overnight
  2. customThe butanol was removed by rotary evaporation
  3. customThe residue obtained
  4. extractionextracted several times with water
  5. dry with materialThe chloroform layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customto give a dark brown oil
  9. washfor elution
  10. customsolvents removed
  11. customA dark brown oil was obtained
  12. customdried in vacuo 2 days at 80° C.

Sources & evidence

ORD record
ord-2a9572346ded4efe8454b7784548446a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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