Reacción #523677

Ecuación de reacción

2-phenyl-3-acetyl benzofuran

paraformaldehyde

diethylamine hydrochloride

hydrogen chloride

→

2-Phenyl-3-[3-(diethylamino)propionyl]benzofuran

Disolventes

isopropanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated at its boiling point
2. 2
   Temperaturaunder reflux for 8 hours
3. 3
   OtroThe solvent was then evaporated from the mixture under vacuum
4. 4
   Otrothe residue was triturated with water
5. 5
   Extracciónthe insoluble portion thereof was extracted
6. 6
   workup.ADDITIONby the addition of a 5% aqueous sodium hydroxide solution
7. 7
   Otrothe oily base which separated
8. 8
   Extracciónwas extracted with ethyl ether
9. 9
   SecadoAfter drying the ether
10. 10
    Extracciónextract over anhydrous sodium sulfate a solution of hydrogen chloride in ethanol
11. 11
    workup.ADDITIONwas added
12. 12
    Otroprecipitated
13. 13
    OtroThe crystals thus obtained
14. 14
    Otrowere recrystallized in a mixture of ethanol and ethyl ether
15. 15
    Otrowas obtained

Procedimiento

To a solution of 47.2 grams of 2-phenyl-3-acetyl benzofuran in 150 milliliters of isopropanol, were added 8.4 grams of paraformaldehyde, 30.8 grams of diethylamine hydrochloride and 3 milliliters of a saturated solution of hydrogen chloride in ethanol and the mixture was heated at its boiling point under reflux for 8 hours. The solvent was then evaporated from the mixture under vacuum and the residue was triturated with water and the insoluble portion thereof was extracted therefrom with ethyl ether. The aqueous solution was made alkaline by the addition of a 5% aqueous sodium hydroxide solution and the oily base which separated was extracted with ethyl ether. After drying the ether extract over anhydrous sodium sulfate a solution of hydrogen chloride in ethanol was added thereto and the crystalline hydrochloride of the compound named in the heading of this example precipitated. The crystals thus obtained were recrystallized in a mixture of ethanol and ethyl ether. In this manner, 34.2 grams of the recrystallized hydrochloride, which had a melting point of 113°-115°C, was obtained.

Fuente