Potassium Iodide → 4'-Tert-butyl-6-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]caprophenone hydrochloride

HRID 267976Notes

Reaction equation

HRID 267976 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.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][Cl:37])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.O>[ClH:37].[C:21]([C:25]1[CH:26]=[CH:27][C:28]([C:31](=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][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:29][CH:30]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 516893Potassium BicarbonateHCID 215529934'-Tert-butyl-6-chlorocaprophenone

Product 1

HCID 215529574'-Tert-butyl-6-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]caprophenone hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 22.4 g (0.08 mole) of α,α-diphenyl-4-piperidinemethanol, 23.8 g (0.09 mole) of 4'-tert-butyl-6-chlorocaprophenone, 20 g (0.2 mole) of potassium bicarbonate, 0.1 g of potassium iodide in 300 ml of toluene and 45 ml of water is stirred on a steam bath for about 96 hours after which 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 4'-tert-butyl-6-[4-(α-hydroxy-α-phenylbenzyl)piperidino]caprophenone hydrochloride.

Workup

  1. customis 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 ether
  6. customThe resulting precipitate is recrystallized from methanol-butanone

Sources & evidence

ORD record
ord-0999aa34735c40f8adce64a580f06ea6
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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