Morpholine → 4-Morpholineacetic acid

HRID 54926

Reaktionsgleichung

Reaktionsgleichung von HRID 54926
Br[CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>O1CCCC1>[O:13]1[CH2:14][CH2:15][N:10]([CH2:2][C:3]([OH:5])=[O:4])[CH2:11][CH2:12]1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 4389684-Morpholineacetic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve t-butyl bromoacetate (leq) in tetrahydrofuran and add morpholine (2.2 eq) via syringe. Stir the reaction mixture at room temperature for 2 hours, filter and wash the filter cake with ethyl acetate. Combine the organic filtrates and wash with saturated sodium bicarbonate (2×), water (2×) and brine. Dry (Na2SO4), filter and evaporate the solvent in vacuo. Take up the oily residue in ethyl acetate, cool in ice and bubble hydrogen chloride gas into the solution. Stir at room temperature overnight, cool and filter to give morpholinoacetic acid (85%); mp 169°-170° C.; 1H NMR (D2O) δ3.75-4.29 (br m, 6), 3.59 (br s, 2), 3.28 (br s, 2).

Aufarbeitung

  1. filtrationfilter
  2. washwash the filter cake with ethyl acetate
  3. washwash with saturated sodium bicarbonate (2×), water (2×) and brine
  4. dry with materialDry (Na2SO4)
  5. filtrationfilter
  6. customevaporate the solvent in vacuo
  7. temperaturecool in ice
  8. custombubble hydrogen chloride gas into the solution
  9. stirringStir at room temperature overnight
  10. temperaturecool
  11. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-41122aec198441e299be45521007238b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624921

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