Potassium Iodide → 4-[4-[alpha-(p-Tert-butylphenyl)-alpha-hydroxybenzyl]piperidino]butyrophenone hydrochloride

HRID 1579327Notes

Reaction equation

HRID 1579327 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[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:25][CH2:26][CH2:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:25].[OH:8][C:7]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:26][CH2:27][CH2:28][C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])[CH2:11][CH2:10]1)([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2535334-ChlorobutyrophenoneHCID 21568357alpha-Phenyl-alpha-(p-tert-butylphenyl)-4-piperidinemethanol

Product 1

HCID 215557314-[4-[alpha-(p-Tert-butylphenyl)-alpha-hydroxybenzyl]piperidino]butyrophenone hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12 g (0.0372 mole) of α-phenyl-α-(p-tert-butylphenyl)-4-piperidinemethanol, 7.85 g (0.042 mole) of 4-chlorobutyrophenone, 13.8 g (0.1 mole) of potassium carbonate, and 0.1 g of potassium iodide in 100 ml of toluene is refluxed with stirring for 64 hours. Upon cooling to room temperature the mixture is filtered, and to the filtrate is added an equal volume of ether followed by treatment with ethereal HCl. The resulting precipitate is recrystallized from isopropyl alcohol and from methanolbutanone to give 4-[4-[α-hydroxy-α-(p-tert-butylphenyl)benzyl]piperidino]butyrophenone hydrochloride, M.P. 228°- 230°C.

Workup

  1. temperatureis refluxed
  2. filtrationis filtered
  3. additionto the filtrate is added an equal volume of ether
  4. customThe resulting precipitate is recrystallized from isopropyl alcohol and from methanolbutanone

Sources & evidence

ORD record
ord-9b1dec6a16224dffb6d005fd86896414
Source dataset
uspto-grants-1976_01
Patent number
US03931197

Reaction notes

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