Hydrochloric Acid → Rimantadine Hydrochloride

HRID 1583455

Reaktionsgleichung

Reaktionsgleichung von HRID 1583455
[CH3:1][C:2]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[N:3]O.[ClH:15]>[Pt].C(O)C>[CH3:1][CH:2]([NH2:3])[C:5]12[CH2:6][CH:7]3[CH2:13][CH:11]([CH2:10][CH:9]([CH2:8]3)[CH2:14]1)[CH2:12]2.[ClH:15]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 2802269HCID 2802269, Verbindung

Produkt 1

HCID 15165Rimantadine HydrochlorideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Into a Parr hydrogenation flask were placed 0.35 g of 5% Pt/C, 1.9 g of 1-adamantyl methyl ketoxime, 230 ml of ethanol and 2.0 ml of conc. hydrochloric acid. The flask was purged with hydrogen and then the hydrogenation reaction was initiated. Pressure was set at 34 psia (234 KPa) at ambient temperature and the reaction conducted overnight. The catalyst was removed by filtration and washed with 50 ml ethanol. The combined ethanol solution was distilled to dryness under vacuum. The remaining white solid was dissolved in 70 ml of water, and extracted twice with 50 ml ether. The ether layer was discarded. The aqueous layer was basified to pH 10-13 with sodium hydroxide and extracted twice with 100 ml of ether. The ether layer was dried over potassium hydroxide and magnesium sulfate which was removed by filtration. The dried ether layer was treated with hydrogen chloride gas and rimantadine hydrochloride precipitated. The solid was collected by filtration and dried to give 1.6 g of rimantadine hydrochloride (75% yield).

Aufarbeitung

  1. customThe flask was purged with hydrogen
  2. customthe hydrogenation reaction
  3. customwas set at 34 psia (234 KPa) at ambient temperature
  4. customThe catalyst was removed by filtration
  5. washwashed with 50 ml ethanol
  6. distillationThe combined ethanol solution was distilled to dryness under vacuum
  7. dissolutionThe remaining white solid was dissolved in 70 ml of water
  8. extractionextracted twice with 50 ml ether
  9. extractionextracted twice with 100 ml of ether
  10. dry with materialThe ether layer was dried over potassium hydroxide and magnesium sulfate which
  11. customwas removed by filtration
  12. additionThe dried ether layer was treated with hydrogen chloride gas and rimantadine hydrochloride
  13. customprecipitated
  14. filtrationThe solid was collected by filtration
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-772f9c2c35ec4b3191a982e130317835
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04551552

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