Lysergic Acid → (+)-Lysergic acid diethylamide

HRID 1007555

Reaktionsgleichung

Reaktionsgleichung von HRID 1007555
[OH:1][C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=O.[C:21](C1NC=CN=1)([C:23]1[NH:24][CH:25]=[CH:26]N=1)=O.C(NCC)C>CN(C)C=O>[CH2:23]([N:24]([CH2:25][CH3:26])[C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=[O:1])[CH3:21]

Komponenten

5

Edukt 3

HCID 6717Lysergic AcidHCID 8021DiethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Produkt 1

HCID 5761(+)-Lysergic acid diethylamideAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 10.0 g (0.037 mol) of d-lysergic acid in 500 ml of dry dimethyl formamide (DMF), under argon, was treated with 9.0 g of carbonyl diimidazole and stirred at room temperature for 1 hour The reaction was then treated with 38 ml of diethylamine and stirred at room temperature overnight. The reaction was concentrated under reduced pressure. The residue was taken up in 500 ml of methylene chloride and washed with 500 ml of water. Insoluble material was removed by filtration and the layers were separated. The organic portion was washed with 250 ml of saturated brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on 800 g of silica gel using 3% methanol in methylene chloride to yield 9.0 g (75%) of d-lysergic acid diethylamide (LSD) as a light brown amorphous solid after evaporation of the solvents.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. concentrationThe reaction was concentrated under reduced pressure
  3. washwashed with 500 ml of water
  4. customInsoluble material was removed by filtration
  5. customthe layers were separated
  6. washThe organic portion was washed with 250 ml of saturated brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on 800 g of silica gel using 3% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-92375b579354429ab7691045676396ce
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794496B2

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