Potassium Iodide → 4'-Cyclopentyl-4-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]butyrophenone hydrochloride

HRID 1579325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579325
[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][C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1)=[O:26].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.O>[ClH:21].[CH:33]1([C:30]2[CH:29]=[CH:28][C:27]([C:25](=[O:26])[CH2:24][CH2:23][CH2:22][N:12]3[CH2:13][CH2:14][CH:9]([C:7]([OH:8])([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:10][CH2:11]3)=[CH:32][CH:31]=2)[CH2:34][CH2:35][CH2:36][CH2:37]1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 516893Potassium BicarbonateHCID 137792534-Chloro-4'-cyclopentylbutyrophenone

Produkt 1

HCID 215683524'-Cyclopentyl-4-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]butyrophenone hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of 27.6 g (0.1 mole) of α,α-diphenyl-4-piperidinemethanol, 30 g (0.12 mole) of 4-chloro-4'-cyclopentylbutyrophenone, 20 g of potassium bicarbonate and 0.1 g of potassium iodide in 250 ml of toluene and 40 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 twice with 50 ml of toluene. The combined organic fractions are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, and filtered. To the filtrate is added two volumes of ether, and the solution is treated with ethereal HCl. The resulting precipitate is collected and recrystallized from methanol-butanone to give 4'-cyclopentyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone hydrochloride, M.P. 232°-234°C.

Aufarbeitung

  1. customis separated
  2. extractionthe aqueous layer is extracted twice with 50 ml of toluene
  3. washThe combined organic fractions are washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. additionTo the filtrate is added two volumes of ether
  7. additionthe solution is treated with ethereal HCl
  8. customThe resulting precipitate is collected
  9. customrecrystallized from methanol-butanone

Quellen und Nachweise

ORD-Eintrag
ord-65064b1c45c344cc80de10238c77a32d
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931197

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