Hydroxylamine → HCID 21708613, Verbindung

HRID 1376495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376495
[C:1](O)(=O)[C:2]([OH:4])=[O:3].Cl[C:8]1([C:16]2[C:17](Cl)=[N:18]S[N:20]=2)[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1.[NH2:22][OH:23].[O:24]=P(Cl)(Cl)Cl.[OH-:29].[Na+]>CO.O>[C:2]([OH:4])(=[O:3])/[CH:1]=[CH:16]/[C:17]([OH:24])=[O:29].[NH2:18][C:17]1[C:16]([CH:8]2[CH:13]3[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]3)[CH2:9]2)=[N:20][O:23][N:22]=1

Komponenten

7

Edukt 4

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21708661HCID 21708661, Verbindung

Produkt 1

HCID 21708613HCID 21708613, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of crude (1-azabicyclo[2.2.21octan-3-yl)hydroxyiminoacetonitrile (10 g, max. 29 mmol) (example 1 C) in methanol (50 ml) was added a methanol solution of hydroxylamine (prepared from NH2OH, HCl (4.2 g, 60 mmol) in methanol (60 ml) and sodium (1.38 g, 60 mmol) in methanol (60 ml)). The reaction mixture was stirred at 40° C. for 18 h and evaporated to give the crude amide oxime derivative. The residue was treated with excess of POCl3 at 45° C. for 18 h. Water and sodium hydroxide was added to obtain alkaline pH and the aqueous mixture extracted with chloroform. The combined organic phases were dried and evaporated to give the free base of the title compound as a solid (yield 570 mg). MS: M+ : 194. Crystallization as the fumarate salt from isopropanol gave the title compound (110 mg) (Compound 66), M.p. 60°-75° C.

Aufarbeitung

  1. customevaporated
  2. customto give the crude amide oxime derivative
  3. customto obtain alkaline pH
  4. extractionthe aqueous mixture extracted with chloroform
  5. customThe combined organic phases were dried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a72d37ab49024f9683927ee459e9c367
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663182

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