Beta-Alanine → N-carboxyethyl-amphetamine

HRID 2372880

Reaktionsgleichung

Reaktionsgleichung von HRID 2372880
[C:1]1([CH2:7][C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[C:14]([CH2:13][CH2:12][NH:11][CH:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:9])([OH:16])=[O:15]

Komponenten

6

Edukt 3

HCID 239Beta-AlanineHCID 7678PhenylacetoneHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 14463243N-carboxyethyl-amphetamineAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Phenylacetone (100 mg, 0.745 mmol) was dissolved in anhydrous methanol (2.0 ml). Beta-alanine (398 mg, 4.47 mmol) was added, followed by sodium cyanoborohydride (94 mg, 1.49 mmol). After 18 hours of stirring under nitrogen, the reaction mixture was filtered, and the filtrate solvent was removed in vacuo. The resulting crude material was purified on four 1.0 millimeter C18 reverse-phase preparative thin layer chromatography plates eluted with H2O/methanol/acetic acid (40/60/0.4). The material obtained was dissolved in ethyl acetate (20 ml) and was extracted with 1.0M sodium bicarbonate (3×20 ml). The aqueous extracts were combined, the pH was adjusted to 4 with 1.0M hydrochloric acid, and the solvent was removed in vacuo. The resulting crystalline solid was then triturated twice with 50-milliliter portions of ethyl acetate and filtered. The filtrates were combined, and the solvent was removed in vacuo to yield 93 milligrams of N-carboxyethyl-amphetamine.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate solvent was removed in vacuo
  3. customThe resulting crude material was purified on four 1.0 millimeter C18 reverse-phase preparative thin layer chromatography plates
  4. washeluted with H2O/methanol/acetic acid (40/60/0.4)
  5. customThe material obtained
  6. extractionwas extracted with 1.0M sodium bicarbonate (3×20 ml)
  7. customthe solvent was removed in vacuo
  8. customThe resulting crystalline solid was then triturated twice with 50-milliliter portions of ethyl acetate
  9. filtrationfiltered
  10. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-672d7e4cf34d4e9999d8f5472e7f45ad
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05101015

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