Dimethylformamide → HCID 60376, Verbindung

HRID 2285725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2285725
Cl.[NH:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:32][CH:33]1[CH2:35][CH2:34]1>O>[CH:33]1([CH2:32][N:2]2[CH2:3][CH:4]=[C:5]([C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=4)[NH:10][CH:9]=3)[CH2:6][CH2:7]2)[CH2:35][CH2:34]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 130190085-Nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole--hydrogen chloride (1/1)

Produkt 1

HCID 60376HCID 60376, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 11.88 g of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-5-nitro-1H-indole hydrochloride, 148 ml of dimethylformamide, 12.72 g of sodium carbonate and 4.8 ml of chloromethylcyclopropane was stirred at 70° C. under an inert atmosphere for 23 hours and the mixture was cooled. 450 ml of distilled water were added to the mixture which was then stirred for one hour and was vacuum filtered. The recovered product was rinsed with water and dried to obtain 10.8 g of raw product. The latter was chromatographed over silica gel and was eluted with a 6-3-1 chloroform-acetone-triethylamine mixture to obtain 8.3 g of 3-(1-cyclopropylmethyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-nitro-1H-indole melting at 187°-188° C.

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. stirringwas then stirred for one hour
  3. filtrationfiltered
  4. washThe recovered product was rinsed with water
  5. customdried
  6. customto obtain 10.8 g of raw product
  7. customThe latter was chromatographed over silica gel
  8. washwas eluted with a 6-3-1 chloroform-acetone-triethylamine mixture

Quellen und Nachweise

ORD-Eintrag
ord-69ab4204c38c4dd0babe9d6f151a630b
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04324790

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