Sodium Iodide → Ethyl 2-acetyl-4-[4-(4-fluorobenzoyl)piperidino]-butyrate

HRID 1461739

Reaktionsgleichung

Reaktionsgleichung von HRID 1461739
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[I-].[Na+].Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1>O1CCCC1>[C:3]([CH:2]([CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([C:23](=[O:31])[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:21][CH2:22]1)[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 10516150Methanone, [1-(2-chloroethyl)-4-piperidinyl](4-fluorophenyl)-

Produkt 1

HCID 14882705Ethyl 2-acetyl-4-[4-(4-fluorobenzoyl)piperidino]-butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 5.45 g of ethyl acetoacetate in 20 ml of tetrahydrofuran is added at 0° C. to a suspension of 1.68 g of sodium hydride at a concentration of 60% in oil in 100 ml of anhydrous tetrahydrofuran. The medium is maintained at 20° C. for 1 hour 30 minutes. 6.3 g of sodium iodide are added, followed by the addition at 0° C. of 11.3 g of 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine in 100 ml of tetrahydrofuran. The reaction mixture is brought to reflux for 15 hours. It is concentrated under vacuum. The residue is taken up in water and the product is extracted with dichloromethane.

Aufarbeitung

  1. temperatureto reflux for 15 hours
  2. concentrationIt is concentrated under vacuum
  3. extractionthe product is extracted with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-eb99b06868674e2c9d29b38620f253b3
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05077288

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