Hydrochloric Acid → Rimantadine

HRID 1583457

Reaktionsgleichung

Reaktionsgleichung von HRID 1583457
[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.Cl>C(O)C.O=[Pt]=O>[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

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 28022691-Adamantan-1-yl-ethanone oxime

Produkt 1

HCID 5071RimantadineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1-Adamantyl methyl ketoxime, 2.0 g, was dissolved in 200 ml of ethanol and mixed with 1.0 ml of conc. hydrochloric acid. This solution was poured into a Parr hydrogenation flask, and 1.0 g of PtO2 was added. Hydrogenation under 35 psia (240 KPa) and at room temperature proceeded slowly. After two days of hydrogenation, the catalyst was removed. The filtrate was distilled to dryness and 100 ml water was added to the residue. The insoluble material was removed by filtration and the aqueous layer was basified with sodium hydroxide. The aqueous layer was extracted with ether and the ether layer was separated. The ether layer was then dried over potassium hydroxide pellets and then magnesium sulfate. The resultant ether solution was distilled to remove the solvent providing 1.0 g rimantadine free base (54% yield).

Aufarbeitung

  1. additionwas added
  2. customat room temperature
  3. customthe catalyst was removed
  4. distillationThe filtrate was distilled to dryness and 100 ml water
  5. additionwas added to the residue
  6. customThe insoluble material was removed by filtration
  7. extractionThe aqueous layer was extracted with ether
  8. customthe ether layer was separated
  9. dry with materialThe ether layer was then dried over potassium hydroxide pellets
  10. distillationThe resultant ether solution was distilled
  11. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-0fa8d051b0f841f0a611983bef9e0083
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04551552

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