Reaktion #533385

Reaktionsgleichung

hydrochloric acid

benzylamine

p-toluenesulfonic acid monohydrate

sodium hydroxide

1-acetyl-4-oxocyclohexyl carboxylic acid ethyl ester

→

4-(Benzylamino)-2-oxobicyclo[2.2.2]octane-1-carboxylic acid ethyl ester

Lösungsmittel

Toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 7 hours with a Dean-Stark apparatus under the dehydration conditions
2. 2
   workup.STIRRINGthe resulting mixture was then stirred for 0.5 hours
3. 3
   Sonstigefollowed by the separation of the organic phase

Vorschrift

Toluene (130 mL) was added to 1-acetyl-4-oxocyclohexyl carboxylic acid ethyl ester (12.9 g, 60.6 mmol) and then the resulting mixture was stirred. To the mixture, there were added benzylamine (13.3 mL, 121 mmol) and p-toluenesulfonic acid monohydrate (124 mg, 0.65 mmol). The mixture was refluxed for 7 hours with a Dean-Stark apparatus under the dehydration conditions. After cooled back to room temperature, a 1 mol/L hydrochloric acid solution (130 mL) was added to the flask and the resulting mixture was then stirred for 0.5 hours. The mixture was made alkali by the use of a 2 mol/L sodium hydroxide aqueous solution, followed by the separation of the organic phase and the subsequent quantitative analysis (according to the LC technique). As a result, the yield of the desired product was found to be 75% (the internal standard substance used was 1,2,4-trimethyl benzene).

Quelle