Sodium Iodide → HCID 21403008, compound

HRID 1730498Notes

Reaction equation

HRID 1730498 reaction equation
[CH3:1][C:2]([OH:15])([CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Cl)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23](=[O:28])[CH2:24][CH2:25][CH2:26][N:12]2[CH2:13][CH2:14][CH:9]([C:2]([OH:15])([CH3:1])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:10][CH2:11]2)=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 54545036HCID 54545036, compound

Product 1

HCID 21403008HCID 21403008, compound

Procedure

The mixture of 2 g of α-methyl-α-(4-piperidyl)-benzyl alcohol, 1.95 g of 4'-fluoro-4-chlorobutyrophenone, 2 g of sodium carbonate (anhydrous), a crystal of sodium iodide and 150 ml of 4-methyl-2-pentanoneare stirred and refluxed for 72 hours. The reaction mixture is filtered to remove the inorganic salts and the filtrate evaporated under reduced pressure. Diethyl ether is added to the residue and the resulting solutionextracted with 5% aqueous hydrochloric acid. The aqueous solution is made basic with ammonia and extracted with diethyl ether. The extract is then dried and evaporated under reduced pressure to afford the 4'-fluoro-4-[4-(α-hydroxy-α-methylbenzyl)-piperidino]-butyrophenone of the formula ##SPC5##

Workup

  1. temperaturerefluxed for 72 hours
  2. filtrationThe reaction mixture is filtered
  3. customto remove the inorganic salts
  4. customthe filtrate evaporated under reduced pressure
  5. additionDiethyl ether is added to the residue
  6. extractionextracted with diethyl ether
  7. customThe extract is then dried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-22246c6e25dc4ad7882b4cf202827d13
Source dataset
uspto-grants-1976_11
Patent number
US03992546

Reaction notes

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