4-Methylmorpholine → 8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one

HRID 41188

Reaktionsgleichung

Reaktionsgleichung von HRID 41188
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]([C:21](OC)=[O:22])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[CH:10][C:9]2=[O:20].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1>O.C(Cl)Cl>[Br:3][C:4]1[CH:5]=[C:6]([C:21]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:22])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[CH:10][C:9]2=[O:20]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 14797Potassium HydroxideHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 58234996methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Produkt 1

HCID 866724148-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-oneAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

KOH (0.419 L, 4889 mmol) was added portionwise to methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate (900 g, 2444 mmol) in water (5 L) at 20° C. over a period of 1 hour. The resulting suspension was stirred at 20° C. for 4 hours until saponification was complete. The reaction was filtered to remove insoluble particles and transferred into a vessel containing water (2 L) (vessel 1). Morpholine (0.639 L, 7333 mmol) was added and agitation continued. 2-chloro-4,6-dimethoxy-1,3,5-triazine (1931 g, 11000 mmol) and water (8 L) was charged to vessel 2 and the temperature adjusted to approximately 7° C., 4-methylmorpholine (134 mL, 1222 mmol) was charged at a rate to maintain the contents at 10° C. and the contents agitated for 4 hours. The contents of vessel 2 was transferred to vessel 1 and agitated at room temperature overnight. DCM (5 L) was then added and the mixture transferred to a 30 litre separator, extracted with a further portion of DCM and the organic extracts combined, dried (Na2SO4) and evaporated to dryness. The solid was stirred in ethyl acetate and filtered to give 8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one (520 g, 50.3%) as a slightly grey solid. Mass Spectrum: m/z [M+H]+=425.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customto remove insoluble particles
  3. customtransferred into a vessel
  4. additioncontaining water (2 L) (vessel 1)
  5. customadjusted to approximately 7° C.
  6. temperatureto maintain the contents at 10° C.
  7. stirringthe contents agitated for 4 hours
  8. customThe contents of vessel 2 was transferred to vessel
  9. stirring1 and agitated at room temperature overnight
  10. extractionextracted with a further portion of DCM
  11. dry with materialdried (Na2SO4)
  12. customevaporated to dryness
  13. stirringThe solid was stirred in ethyl acetate
  14. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-0d5dde077d994d618b629f9efa9dedd6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530470B2

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