Morpholine → (1H-Indol-6-yl)(morpholino)methanone

HRID 1685558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685558
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=2)[CH:3]=[CH:2]1.[C:13](C1NC=CN=1)([C:15]1N[CH:17]=[CH:18][N:19]=1)=[O:14].N1CCOCC1>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([N:19]3[CH2:15][CH2:13][O:14][CH2:17][CH2:18]3)=[O:12])[CH:8]=2)[CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 5952301H-indole-6-carboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Produkt 1

HCID 39710543(1H-Indol-6-yl)(morpholino)methanoneAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Indole-6-carboxylic acid (0.60 g, 3.7 mmol) was dissolved in DCM (15 mL) and carbonyl diimidazole (0.63 g, 3.9 mmol) was added and the reaction mixture was refluxed under N2 for 30 min. The mixture was allowed to cool to room temperature before morpholine (0.39 g, 4.5 mmol) was added and the reaction mixture was refluxed for 16 hours. The mixture was allowed to cool to room temperature before it was washed in sequence with HCl (50 mL, 1 N in water), NaOH (50 mL, 1 N in water) and brine (50 mL). The organic phase was dried with MgSO4, and the solvent was removed in vacuo to give 0.74 g of (1H-indol-6-yl)-morpholin-4-yl-methanone.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed under N2 for 30 min
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for 16 hours
  4. washwas washed in sequence with HCl (50 mL, 1 N in water), NaOH (50 mL, 1 N in water) and brine (50 mL)
  5. dry with materialThe organic phase was dried with MgSO4
  6. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-968c67c9de044af7b33e23badd508a5c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148413B2

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