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

HRID 267975

Reaction equation

HRID 267975 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][CH:31]=[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][CH:31]=[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 703385-Chloro-1-phenyl-1-pentanoneHCID 516893Potassium Bicarbonate

Product 1

HCID 215529985-[4-(alpha-Hydroxy-alpha-phenylbenzyl)piperidino]valerophenone hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 27.6 g (0.1 mole) of α,α-diphenyl-4-piperidinemethanol, 21.6 g (0.11 mole) of 5-chlorovalerophenone, 20 g of potassium bicarbonate, and 0.1 g of potassium iodide in 300 ml of toluene and 25 ml of water is stirred and refluxed for 136 hours then worked up by the procedure described in Examples 2 and 3 to give 5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone hydrochloride, M.P. 162°-164°C.

Workup

  1. temperaturerefluxed for 136 hours

Sources & evidence

ORD record
ord-ecdb1a75e63c4c2685b929b1aa626727
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Linked notes

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