Dimethylformamide → 1-Ethyl-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 851141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851141
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7](I)[CH3:8].Cl.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][NH:21][CH2:22][CH2:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1.CN(C)C=O>O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][N:21]([CH2:7][CH3:8])[CH2:22][CH2:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 130667493-(3-Methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride

Produkt 1

HCID 205026301-Ethyl-5-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

9.8 g of sodium carbonate and 2.6 ml of ethyl iodide were added to a suspension of 7 g of 3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine hydrochloride and 70 ml of dimethylformamide and the mixture was stirred for 16 hours and was diluted with water. The mixture was extracted with ethyl acetate and the organic extract was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-1-1 cyclohexane-chloroform-triethylamine mixture to obtain 5.3 g of 3-(3-methoxyphenyl)-1-ethyl-1,2,5,6-tetrahydropyridine.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionthe organic extract
  3. washwas washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washwas eluted with an 8-1-1 cyclohexane-chloroform-triethylamine mixture

Quellen und Nachweise

ORD-Eintrag
ord-4076ac29e63249169542e3ef4b07f737
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382942

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