Potassium Carbonate → 1,2,5,6-Tetrahydro-1-(4,4-diphenyl-3-butenyl)-3-pyridinecarboxylic acid methyl ester hydrochloride

HRID 851299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851299
[ClH:1].[CH3:2][O:3][C:4]([C:6]1[CH2:7][NH:8][CH2:9][CH2:10][CH:11]=1)=[O:5].[C:12]1([C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH2:20][CH2:21]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[ClH:1].[CH3:2][O:3][C:4]([C:6]1[CH2:7][N:8]([CH2:21][CH2:20][CH:19]=[C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:9][CH2:10][CH:11]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 201540Norarecoline HydrochlorideHCID 104017744,4-Diphenyl-3-butenyl bromide

Produkt 1

HCID 704835431,2,5,6-Tetrahydro-1-(4,4-diphenyl-3-butenyl)-3-pyridinecarboxylic acid methyl ester hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 5.0 g. (0.0282 mole) of 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester, hydrochloride, 8.08 g. (0.282 mole) of 4,4-diphenyl-3-butenyl bromide and 10 g. of crushed potassium carbonate was refluxed in 200 ml. of acetone for 15 hours. The reaction mixture was evaporated, extracted into ethyl acetate from water, dried, evaporated and chromatographed on silica (dry column) eluted with hexane/hexane:ethyl acetate to give 1,2,5,6-tetrahydro-1-(4,4-diphenyl-3-butenyl)-3-pyridinecarboxylic acid methyl ester hydrochloride.

Aufarbeitung

  1. additionA mixture of 5.0 g
  2. customThe reaction mixture was evaporated
  3. extractionextracted into ethyl acetate from water
  4. customdried
  5. customevaporated
  6. customchromatographed on silica (dry column)
  7. washeluted with hexane/hexane

Quellen und Nachweise

ORD-Eintrag
ord-773d2e2948554465a5cd2519b28d69e4
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04383999

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