Piperidine → 3-[2-(6-Morpholin-4-yl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]propionic acid

HRID 1860926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860926
[N:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:17]([C:19]1[NH:20][C:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=2[C:27]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=O.N1CCCCC1>C(O)C>[N:1]1([C:7]2[CH:15]=[C:14]3[C:10]([C:11](=[CH:17][C:19]4[NH:20][C:21]5[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=5[C:27]=4[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acidHCID 219256916-(Morpholin-4-yl)-2-oxindole

Produkt 1

HCID 697649383-[2-(6-Morpholin-4-yl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]propionic acidAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4 g of 6-(morpholin-4-yl)-2-oxindole, 3.75 g of 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid, and 1.8 mL of piperidine in ethanol (60 mL) was refluxed for 6 hrs. The reaction mixture was concentrated and acidified with 6 N hydrochloric acid to pH 6. The precipitate was collected by filtration, washed once with water, twice with ethyl acetate and twice with methanol to give 2.6 g of 3-[2-(6-Morpholin-4-yl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]propionic acid as an orange solid (34% yield).

Aufarbeitung

  1. temperaturewas refluxed for 6 hrs
  2. concentrationThe reaction mixture was concentrated
  3. filtrationThe precipitate was collected by filtration
  4. washwashed once with water, twice with ethyl acetate and twice with methanol

Quellen und Nachweise

ORD-Eintrag
ord-15d412cd915b4d0199c4143af0731149
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

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