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Potassium Iodide → 4'-Tert-butyl-4-[4-[alpha-hydroxy-alpha-(p-tolyl)benzyl]-piperidino]butyrophenone hydrochloride

HRID 1579326
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1579326
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[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:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:37])[CH2:33][CH2:34][CH2:35][Cl:36])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.O>[ClH:36].[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:32](=[O:37])[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][C:18]([CH3:21])=[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:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 516893Potassium BicarbonateHCID 27236944'-tert-Butyl-4-chlorobutyrophenoneHCID 21568361alpha-Phenyl-alpha-(p-tolyl)-4-piperidinemethanol

Produkt 1

HCID 215683424'-Tert-butyl-4-[4-[alpha-hydroxy-alpha-(p-tolyl)benzyl]-piperidino]butyrophenone hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of 29.0 g (0.1 mole) of α-phenyl-α-(p-tolyl)-4-piperidinemethanol, 32 g (0.12 mole) of 4'-tert-butyl-4-chlorobutyrophenone, 20 g of potassium bicarbonate, 0.1 g of potassium iodide, 300 ml of toluene and 50 ml of water is stirred on a steam bath for 88 hours. Upon cooling to room temperature the toluene layer is separated, and the aqueous layer is extracted with toluene. The combined toluene fractions are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to an oil. The oily residue is dissolved in dry ether and filtered. The filtrate is treated with ethereal HCl, and the resulting precipitate is collected and recrystallized from methanol-butanone to give 4'-tert-butyl-4-[4-[α-hydroxy-α-(p-tolyl)benzyl]-piperidino]butyrophenone hydrochloride, M.P. 194°-196.5°C.

Aufarbeitung

  1. customis separated
  2. extractionthe aqueous layer is extracted with toluene
  3. washThe combined toluene fractions are washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. dissolutionThe oily residue is dissolved in dry ether
  8. filtrationfiltered
  9. additionThe filtrate is treated with ethereal HCl
  10. customthe resulting precipitate is collected
  11. customrecrystallized from methanol-butanone

Quellen und Nachweise

ORD-Eintrag
ord-70a8fd652fee4eeda76ee9724cbc3fc0
Quelldatensatz
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03931197

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