Sodium Iodide → HCID 21403008, compound

HRID 972912Notes

Reaction equation

HRID 972912 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+]>CC(C)CC(=O)C>[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

6

Reactant 4

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

Product 1

HCID 21403008HCID 21403008, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

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-pentanone are 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 solution extracted 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 ##STR5## Recrystallization from isopropanol yields the above compound melting at 55°-57° and isolated as a solvate.

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. extractionthe resulting solution extracted with 5% aqueous hydrochloric acid
  7. extractionextracted with diethyl ether
  8. customThe extract is then dried
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2406ff01448b4d3bab99bac9f3a18ca3
Source dataset
uspto-grants-1977_10
Patent number
US04054570

Reaction notes

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