Potassium Carbonate → Isopropyl [4-(diphenylmethylidene)piperidin-1-yl]ethanoate

HRID 2250413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250413
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH2:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetateHCID 27625334-(Diphenylmethylene)piperidine

Produkt 1

HCID 10225202Isopropyl [4-(diphenylmethylidene)piperidin-1-yl]ethanoateAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of amine 20 (779 mg, 3.12 mmol), isopropyl bromoacetate (575 mg, 3.18 mmol), K2CO3 (1.34 g, 3 eq), and acetonitrile (28 mL) was stirred at reflux overnight. The reaction mixture was filtered, evaporated to dryness, and then chromatographed over silica gel using 5:1 heptane/EtOAc to give 0.78 g of 15d as an oil that crystallized on standing. The structure was confirmed by 1H NMR. (Acetate esters 15b and 15c were similarly prepared.)

Aufarbeitung

  1. temperatureat reflux overnight
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. customchromatographed over silica gel using 5:1 heptane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c39ae4af55b847a0a1973beff33c29ed
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317026B2

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