Potassium Carbonate → 4-[1-(2-propenyl)-1,2,5,6-tetrahydropyridin-3-yl]-1H-indole

HRID 1155691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155691
[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][C:6]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)(O)[CH2:5]1)[CH:2]=[CH2:3].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>Cl>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]=[C:6]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH2:5]1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 20537467HCID 20537467, Verbindung

Produkt 1

HCID 30683594-[1-(2-propenyl)-1,2,5,6-tetrahydropyridin-3-yl]-1H-indoleAusbeute 52,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of 14 g of the product of Example 27 in 400 ml of hydrochloric acid was refluxed for 4 hours and the mixture was iced and made alkaline with sodium hydroxide. Potassium carbonate was added to the mixture which was then extracted with ethyl acetate. The organic phase was dried and evaporated to dryness under reduced pressure and the 12.7 g of residue were chromatographed over silica gel. Elution with a 9-1 chloroform-acetone mixture yielded 6.85 g of 4-[1-(2-propenyl)-1,2,5,6-tetrahydropyridin-3-yl]-1H-indole with an Rf=0.15.

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated to dryness under reduced pressure
  4. customthe 12.7 g of residue were chromatographed over silica gel
  5. washElution with a 9-1 chloroform-acetone mixture

Quellen und Nachweise

ORD-Eintrag
ord-5d27f942fd284967bc86634873cf0df3
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04332808

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