Azacyclonol → Methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate hydrochloride

HRID 1018101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1018101
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=1)=[O:6].[C:20]1([C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[OH:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[ClH:1].[OH:27][C:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=2)=[O:6])[CH2:30][CH2:29]1

Komponenten

4

Edukt 2

HCID 15723AzacyclonolHCID 10062338Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate

Produkt 1

HCID 22471930Methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate hydrochlorideAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Dissolve 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid, methyl ester (2.82 g, 10.0 mmol) and α,α-diphenyl-4-piperidinemethanol (5.58 g, 21.0 mmol) in toluene (20 mL). Reflux for 29 hours, cool in an ice bath, filter, filter the filtrate though silica gel (5 g) and wash the gel with toluene (10 mL). Evaporate the solvent in vacuo and dissolve the residue in ethyl ether (100 mL). Add anhydrous hydrogen chloride and filter to give the title compound as an off-white powder (4.2 g, 76%); mp 165-175° C.

Aufarbeitung

  1. temperatureReflux for 29 hours
  2. temperaturecool in an ice bath
  3. filtrationfilter
  4. filtrationfilter the filtrate though silica gel (5 g)
  5. washwash the gel with toluene (10 mL)
  6. customEvaporate the solvent in vacuo
  7. dissolutiondissolve the residue in ethyl ether (100 mL)
  8. filtrationAdd anhydrous hydrogen chloride and filter

Quellen und Nachweise

ORD-Eintrag
ord-e35bbff9af384c549aca15808c6e9926
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479663B2

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