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Potassium Carbonate → Oxiracetam

HRID 2291685
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2291685
Cl.CC(C1[NH:9][C:8](=[O:10])[CH2:7][NH:6]1)C.N1C2(CCCCC2)NCC1=O.C(=O)([O-])[O-].[K+].[K+].[O:28]1[CH2:36][CH:29]1[CH2:30][C:31]([O:33]CC)=O>O.CN(C=O)C.CC(C)=O>[CH2:30]1[C:31](=[O:33])[N:6]([CH2:7][C:8]([NH2:9])=[O:10])[CH2:36][CH:29]1[OH:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 9898830Ethyl 2-(oxiran-2-yl)acetateHCID 131250391,4-Diazaspiro[4.5]decan-2-oneHCID 212792932-(1-Methylethyl)-4-imidazolidinone hydrochloride

Produkt 1

HCID 4626OxiracetamAusbeute 6,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180
Acetone
Lösungsmittel
HCID 962WaterLösungsmittel2×
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

5.8 g of 2-(1-methylethyl)-4-imidazolidinone hydrochloride ((5); R4 =H, R5 =isopropyl) (0.035 moles) are shaken in 10 ml water and treated with 2.4 g potassium carbonate (0.0174 moles). 4.5 g ethyl 3,4-epoxybutanoate and 6 ml acetone are added, and stirring is maintained for 45 h at 70° C. After evaporation, the residue is chromatographed on silica, eluting with 8:2 ethyl acetate/methanol. The main fractions are collected and evaporated. The oil that remains is taken up with ethyl acetate. After being left to stand overnight the white compound obtained is filtered: 1.3 g ethyl 2-(1-methylethyl)-4-oxo-1-imidazolidine-β-hydroxybutanoate m.p. 118°-122° C. 0.95 g of this compound (3.7 mmoles) are heated to boiling for 15 h in 4 ml DMF and 1 ml water. After evaporation in vacuo, the residue is taken up with methanol, and the solution is filtered. 0.37 g oxiracetam is obtained as a white crystalline powder, m.p. 167°-70° C. (63.2%).

Aufarbeitung

  1. customAfter evaporation
  2. customthe residue is chromatographed on silica
  3. washeluting with 8:2 ethyl acetate/methanol
  4. customThe main fractions are collected
  5. customevaporated
  6. waitAfter being left
  7. customthe white compound obtained
  8. filtrationis filtered
  9. customAfter evaporation in vacuo
  10. filtrationthe solution is filtered

Quellen und Nachweise

ORD-Eintrag
ord-433dbce7844045909b2be15176cc5b83
Quelldatensatz
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04797496

Notizen zur Reaktion

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