Hydrochloric Acid → 2-[4-(4-Fluorobenzoyl)piperidin-1-yl]-1-(naphthalen-2-yl)ethan-1-one--hydrogen chloride (1/1)

HRID 1649778Notes

Reaction equation

HRID 1649778 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[ClH:15].[F:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1.[I-].[K+].C(=O)([O-])O.[Na+].Cl>C(O)C>[ClH:15].[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:2][C:3]([C:5]3[CH:14]=[CH:13][C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:6]=3)=[O:4])[CH2:25][CH2:24]2)=[O:22])=[CH:29][CH:30]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 691792-Bromo-2'-acetonaphthoneHCID 516892Sodium BicarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 1296862-[4-(4-Fluorobenzoyl)piperidin-1-yl]-1-(naphthalen-2-yl)ethan-1-one--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

49.7 g of 2-bromo-2'-acetonaphthone, 49.9 g of 4-(p-fluorobenzoyl)piperidine hydrochloride, 0.5 g of potassium iodide and 50.4 g of sodium hydrogencarbonate were added to 500 ml of ethanol and the mixture was refluxed for 2 h. The solvent was distilled off and chloroform was added to the residue. The mixture was washed with water and dried. Chloroform was distilled off and the residue was purified according to silica gel column chromatography to obtain 58.9 g of the crystalline intended product, which was converted into its hydrochloride and recrystallized by an ordinary process to obtain the intended hydrochloride.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. distillationThe solvent was distilled off
  3. additionchloroform was added to the residue
  4. washThe mixture was washed with water
  5. customdried
  6. distillationChloroform was distilled off
  7. customthe residue was purified
  8. customto obtain 58.9 g of the
  9. customrecrystallized by an ordinary process

Sources & evidence

ORD record
ord-a7019932ba8b412d96a03fb8fc975906
Source dataset
uspto-grants-1990_05
Patent number
US04921863

Reaction notes

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