Formic Acid → Methylephedrine

HRID 1649589

Reaktionsgleichung

Reaktionsgleichung von HRID 1649589
[CH3:1][C@H:2]([NH:11][CH3:12])[C@H:3]([OH:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.Cl.[OH-].[Na+].[CH:16](O)=O.C=O>O>[CH3:1][C@H:2]([N:11]([CH3:16])[CH3:12])[C@H:3]([OH:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 65326Ephedrine Hydrochloride

Produkt 1

HCID 64782Methylephedrine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Ephedrine hydrochloride (30.3 g, 0.15 mol) was dissolved in warm water (60 ml) there was, then added thereto a 40% sodium hydroxide aqueous solution (15 ml, 0.15 mol) and 85% formic acid (21.7 g, 0.4 mol) and the mixtures refluxed under heating, and to this solution was added dropwise a 35% formalin solution (15 g, 0.18 mol) over 20 minutes. Thereafter, refluxing under heating was continued for 3 hours and the reaction solution was concentrated to 1/2 of its original volume and then added thereto was a 40% sodium hydroxide aqueous solution to adjust the pH to about 11. The resultant precipitated crystals were filtered out and recrystallized from methanol. Yield: 23 g (84%); m.p.: 86.5°-87.5° C. [α]D20 =-29.5° (C=4.54, MeOH).

Aufarbeitung

  1. additionadded
  2. temperatureunder heating
  3. temperatureThereafter, refluxing
  4. temperatureunder heating
  5. concentrationthe reaction solution was concentrated to 1/2 of its original volume
  6. additionadded
  7. customThe resultant precipitated crystals
  8. filtrationwere filtered out
  9. customrecrystallized from methanol
  10. customm.p.: 86.5°-87.5° C. [α]D20 =-29.5° (C=4.54, MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-815e004e40254dbe81c7fcaf9c975521
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04418218

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