Potassium Iodide → HCID 21552950, compound

HRID 267972Notes

Reaction equation

HRID 267972 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:37])[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:36].[C:21]([C:25]1[CH:26]=[CH:27][C:28]([C:31](=[O:37])[CH2:32][CH2:33][CH2:34][CH2:35][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

6

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 516893Potassium BicarbonateHCID 14268798HCID 14268798, compound

Product 1

HCID 21552950HCID 21552950, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 32.0 g (0.12 mole) of α,α-diphenyl-4-piperidinemethanol, 38.0 g (0.15 mole) of 4'-tert-butyl-5-chlorovalerophenone, 27.8 g (0.2 mole) of potassium bicarbonate, and 200 mg of potassium iodide in about 500 ml of toluene is stirred and refluxed for 142 hours then filtered while hot. About 50 ml of ether is added to the filtrate which is then made acidic using ethereal HCl. The resulting precipitate is recrystallized from methanol-butanone to give 4'-tert-butyl-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone hydrochloride, M.P. 209.5°-211°C.

Workup

  1. temperaturerefluxed for 142 hours
  2. filtrationthen filtered while hot
  3. additionAbout 50 ml of ether is added to the filtrate which
  4. customThe resulting precipitate is recrystallized from methanol-butanone

Sources & evidence

ORD record
ord-c9eaa05fda04402aa60c80c9b622c073
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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