Sodium Iodide → HCID 86735143, compound

HRID 972915Notes

Reaction equation

HRID 972915 reaction equation
[OH:1][C:2]([C:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH:12]=1)([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:29])[CH2:25][CH2:26][CH2:27]Cl)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(C)CC(=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24](=[O:29])[CH2:25][CH2:26][CH2:27][N:14]2[CH2:15][CH2:16][C:11]([C:2]([OH:1])([CH3:10])[C:3]3[CH:4]=[CH:5][C:6]([F:9])=[CH:7][CH:8]=3)=[CH:12][CH2:13]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 21403011HCID 21403011, compound

Product 1

HCID 86735143HCID 86735143, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2.0 g of 4-(α-hydroxy-α-methyl-4-fluorobenzyl)-1,2,5,6-tetrahydropyridine, 2.5 g of 4'-fluoro-4-chlorobutyrophenone, 3.0 g of sodium carbonate, a crystal of sodium iodide, in 100 ml of 4-methyl-2-pentanone is stirred and refluxed for 72 hours. It is cooled, filtered, and the filtrate evaporated under reduced pressure. Diethyl ether is added to the residue and the resulting solution extracted with 5% aqueous hydrochloric acid. The aqueous solution is made basic with ammonium hydroxide and extracted with diethyl ether. The extract is dried, evaporated and the residue recrystallized from isopropanol, to give the 4'-fluoro-4-[4-(α-hydroxy-α-methyl-4-fluorobenzyl)-1,2,5,6-tetrahydropyridyl]-butyrophenone melting at 95°.

Workup

  1. temperaturerefluxed for 72 hours
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure
  5. additionDiethyl ether is added to the residue
  6. extractionthe resulting solution extracted with 5% aqueous hydrochloric acid
  7. extractionextracted with diethyl ether
  8. customThe extract is dried
  9. customevaporated
  10. customthe residue recrystallized from isopropanol

Sources & evidence

ORD record
ord-548d8fa411f5450a980fbde6e545d225
Source dataset
uspto-grants-1977_10
Patent number
US04054570

Reaction notes

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