Reaktion #58514

Reaktionsgleichung

sodium cyanoborohydride

5-[1-(4-amino-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester

m-tolualdehyde

ammonium chloride

→

5-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester

Ausbeute 43.0%

Lösungsmittel

THF

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 1 h
3. 3
   SonstigeThe solvent was evaporated
4. 4
   ExtraktionThe aqueous phase was extracted with dichloromethane
5. 5
   Trocknenthe combined organic phases were dried over magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated

Vorschrift

A mixture of 304.0 mg (1.0 mmol) 5-[1-(4-amino-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester, 120.0 mg (1.0 mmol) m-tolualdehyde and 2 ml ethanol was heated under reflux for 1 h. The solvent was evaporated and 3 ml THF and 315 mg (5.0 mmol) sodium cyanoborohydride were added to the residue. After 18 h 5 ml aqueous ammonium chloride solution and 10 ml water were added. The aqueous phase was extracted with dichloromethane, the combined organic phases were dried over magnesium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (ethyl acetate/petrol ether 1:1) to yield 175 mg (0.43 mmol) 5-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester.

Quelle