Potassium Iodide → HCID 9869815, compound

HRID 1368898Notes

Reaction equation

HRID 1368898 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8].Cl.[CH2:17]1[C:22]2[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[O:25][C:21]=2[CH2:20][CH2:19][NH:18]1.[C:30]([O-:33])([O-:32])=O.[Na+].[Na+].[I-].[K+]>C(C(C)=O)C(C)C>[C:7]([OH:25])(=[O:8])/[CH:9]=[CH:14]/[C:30]([OH:33])=[O:32].[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:18]2[CH2:19][CH2:20][C:21]3[O:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[C:22]=3[CH2:17]2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 118170476-Chloro-1-(4-fluorophenyl)hexan-1-oneHCID 124995131,2,3,4-Tetrahydrobenzo-furo[3,2-c]pyridine hydrochloride

Product 1

HCID 9869815HCID 9869815, compoundYield 141.2%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 6-chloro-1-(4-fluorophenyl)-1-hexanone (0.018 mol), intermediate 1 (0.015 mol), Na2CO3 (4 g) and potassium iodide (catalytic quantity) in methyl isobutyl ketone (200 ml) was stirred and refluxed overnight and then cooled to room temperature. The solvent was evaporated. The residue was washed with H2O and the mixture was extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was converted into the (E)-2-butenedioic acid salt (1:1); The precipitate was filtered off and dried, yielding 5.1 g 1-(4-fluorophenyl)-6-(1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-2-yl)-1-hexanone (E)-2-butenedioate (1:1) (71%).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. washThe residue was washed with H2O
  4. extractionthe mixture was extracted with CH2Cl2
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-1e3a66e7cc1b46e291f0aad392bca7e7
Source dataset
uspto-grants-2003_06
Patent number
US06576640B1

Reaction notes

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