Potassium Iodide → 5-[4-(alpha-Hydroxy-alpha-phenylbenzyl)piperidino]-4'-methoxyvalerophenone hydrochloride

HRID 267974Notes

Reaction equation

HRID 267974 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]([O:34][CH3:35])=[CH:30][CH:29]=1)=[O:27].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.O>[ClH:21].[OH:8][C:7]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[O:27])[CH2:11][CH2:10]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 516893Potassium BicarbonateHCID 127094845-Chloro-1-(4-methoxyphenyl)pentan-1-one

Product 1

HCID 215529465-[4-(alpha-Hydroxy-alpha-phenylbenzyl)piperidino]-4'-methoxyvalerophenone hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 41.5 g (0.15 mole) of α,α-diphenyl-4-piperidinemethanol, 38.6 g (0.17 mole) of 5-chloro-4'-methoxyvalerophenone, 30 g of potassium bicarbonate, and 0.19 g of potassium iodide in 500 ml of toluene and 70 ml of water is stirred and refluxed for 136 hours. The organic layer is separated and combined with 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 ether and made acidic with ethereal HCl. The resulting precipitate is recrystallized from methanol-butanone to give 5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'-methoxyvalerophenone hydrochloride, M.P. 211°-213°C.

Workup

  1. temperaturerefluxed for 136 hours
  2. customThe organic layer is separated
  3. washThe combined organic material is washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. additionThe filtrate is diluted with ether
  7. customThe resulting precipitate is recrystallized from methanol-butanone

Sources & evidence

ORD record
ord-5f82da794b7c497daec4e7919d014cae
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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