Water → 2,2,2-trichloroethyl 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,2,5,6-tetrahydro-pyridinecarboxylate

HRID 2294068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294068
[CH2:1]([C:4]1([C:19]2[CH2:24][CH2:23][N:22](C)[CH2:21][CH:20]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].[Cl:26][C:27]([Cl:34])([Cl:33])[CH2:28][O:29][C:30](Cl)=[O:31].O>C1C=CC=CC=1>[CH2:1]([C:4]1([C:19]2[CH2:24][CH2:23][NH:22][CH:21]([C:30]([O:29][CH2:28][C:27]([Cl:34])([Cl:33])[Cl:26])=[O:31])[CH:20]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 870632,2,2-Trichloroethyl chloroformateHCID 97975634-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1-methyl-1,2,5,6-tetrahydropyridine

Produkt 1

HCID 214741302,2,2-trichloroethyl 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,2,5,6-tetrahydro-pyridinecarboxylateAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Dissolved 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1-methyl-1,2,5,6-tetrahydropyridine (3.3 g, 10.0 mmol) in 50 mL of benzene, and added 2,2,2-trichloroethylchloroformate (3.0 mL, 4.6 g, 21.8 mmol). Refluxed for 20 hours under a nitrogen atmosphere. Cooled to room temperature, and added water. Extracted with ether. Dried combined organic extracts with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with dichloromethane. Combined appropriate fractions, and evaporated to give 3.7 g (75% yield) of 2,2,2-trichloroethyl 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,2,5,6-tetrahydro-pyridinecarboxylate as an oil.

Aufarbeitung

  1. temperatureRefluxed for 20 hours under a nitrogen atmosphere
  2. extractionExtracted with ether
  3. customDried
  4. filtrationfiltered
  5. customevaporated
  6. customPurified crude product by flash chromatography on silica gel eluting with dichloromethane
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3921e35a590f4c21afed5fa9ee6f2414
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688805

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