Carnitine Chloride → Norcarnitine

HRID 745675

Reaktionsgleichung

Reaktionsgleichung von HRID 745675
[CH3:1][N+:2]([CH2:5][CH:6]([OH:11])[CH2:7][C:8]([OH:10])=[O:9])(C)[CH3:3].[Cl-].N12CCN(CC1)CC2>CN(C=O)C>[CH3:1][N:2]([CH2:5][C@H:6]([OH:11])[CH2:7][C:8]([OH:10])=[O:9])[CH3:3]

Komponenten

4

Edukt 2

HCID 5970Carnitine ChlorideHCID 9237Dabco

Produkt 1

HCID 3081992Norcarnitine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

L-carnitine chloride (1.5. g; 0.008 moles) and 1,4 diazabicyclo[2,2,2]octane (5.25 g; 0.05 moles) were dissolved in 50 cc of DMF at 80° C. The resulting solution was subsequently heated up to 125° C. for 2 hours. Upon reaction termination, the solution was cooled in an ice bath a 5° C. After about 2 hours the precipitate which formed consisting of the excess diazabicyclo octane and its N-methyl derivative was filtered off. DMF was distilled under vacuum and the residue dissolved in water and eluted on AMBERLITE IRA 402 resin activated in the OH-l form. The eluate having alkaline pH was shown to consist of diazabicyclo octane and its N-methyl derivative; L-norcarnitine which formed was retained on the resin and was eluted therefrom with 2N HCl.

Aufarbeitung

  1. customUpon reaction termination
  2. temperaturethe solution was cooled in an ice bath a 5° C
  3. customAfter about 2 hours the precipitate which formed
  4. filtrationwas filtered off
  5. distillationDMF was distilled under vacuum
  6. dissolutionthe residue dissolved in water
  7. washeluted on AMBERLITE IRA 402 resin

Quellen und Nachweise

ORD-Eintrag
ord-4b7a83338cdf4bc8aacd50edcdfc5d19
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04599447

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