Potassium Iodide → 4'-Fluoro-5-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]valerophenone hydrochloride

HRID 267973Notes

Reaction equation

HRID 267973 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:27].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.O>[ClH:21].[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][N:12]2[CH2:13][CH2:14][CH:9]([C:7]([OH:8])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:10][CH2:11]2)=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 516893Potassium BicarbonateHCID 126497945-Chloro-1-(4-fluorophenyl)-1-oxopentane

Product 1

HCID 215529524'-Fluoro-5-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]valerophenone hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 19.3 g (0.07 mole) of α,α -diphenyl-4-piperidinemethanol, 17.1 g (0.08 mole) of 5-chloro-4'-fluorovalerophenone, 20.0 g (0.2 mole) of potassium bicarbonate, and 0.1 g of potassium iodide in 250 ml of toluene and 35 ml of water is stirred on a steam bath for 70 hours. The organic layer is separated and combined with two 50 ml toluene extracts of the aqueous layer. The combined organic material is washed with water and saturated sodium chloride solution, dried over magnesium sulfate and filtered. The filtrate is diluted with about 200 ml of ether then made acidic with ethereal HCl. The resulting precipitate is recrystallized from methanol-butanone to give 4'-fluoro-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone hydrochloride, M.P. 177°-179°C.

Workup

  1. customThe organic layer is separated
  2. washThe combined organic material is washed with water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. additionThe filtrate is diluted with about 200 ml of ether
  6. customThe resulting precipitate is recrystallized from methanol-butanone

Sources & evidence

ORD record
ord-e7775154740c442a8bdbdf18ccfcf47a
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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