Ammonium Hydroxide → 1,2,3,4-Tetrahydro-5H-[1,3]benzodioxolo[5',6':5,6]pyrano[3,4-c]pyridin-5-one hydrochloride

HRID 851184

Reaktionsgleichung

Reaktionsgleichung von HRID 851184
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.[ClH:11].O=[C:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH:14]1[C:19](OC)=[O:20].[OH-].[NH4+]>S(=O)(=O)(O)O>[ClH:11].[CH2:18]1[CH2:17][NH:16][CH2:15][C:14]2[C:19](=[O:20])[O:10][C:5]3[CH:4]=[C:3]4[C:8]([O:9][CH2:1][O:2]4)=[CH:7][C:6]=3[C:13]1=2

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 68289SesamolHCID 2724028Methyl 4-oxopiperidine-3-carboxylate hydrochloride

Produkt 1

HCID 131369091,2,3,4-Tetrahydro-5H-[1,3]benzodioxolo[5',6':5,6]pyrano[3,4-c]pyridin-5-one hydrochlorideAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A mixture of 3,4-methylenedioxyphenol (125 g, 0.91 moles) and methyl 4-oxo-3-piperidinecarboxylate hydrochloride (125 g, 0.65 moles) is cooled in ice and treated over one hour with 600 ml of 72% sulfuric acid. The mixture is then stirred at room temperature for 64 hours. Ice/water (1.0 kg) is added, followed by conc. ammonium hydroxide, until the pH of the mixture is 9.0. The crude product is filtered, stirred briefly in 2.5% aqueous sodium hydroxide (1.0 l), and refiltered. Several recrystallizations from dilute aqueous hydrochloric acid yielded the product (86.2 g) as the hydrochloride, mp 258°-259° C.

Aufarbeitung

  1. temperatureis cooled in ice
  2. filtrationThe crude product is filtered
  3. stirringstirred briefly in 2.5% aqueous sodium hydroxide (1.0 l)
  4. customSeveral recrystallizations from dilute aqueous hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-bbc84d6a2fe8407b92b35db6104829f2
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382939

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