Reacción #83608

Ecuación de reacción

NaHCO3

2-bromo-1-(4-fluorophenylmethyl)-1H-benzimidazole

1-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane

→

5-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane

Rendimiento 85.0%

Disolventes

n-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 2 hours
2. 2
   Extracciónthe mixture was extracted with methylene chloride (30 ml)
3. 3
   LavadoThe extract was washed with water
4. 4
   Secadodried over anhydrous MgSO4
5. 5
   OtroThe solvent was removed under reduced pressure
6. 6
   Otrothe residue was purified by medium pressure liquid column chromatography on a silica gel column
7. 7
   workup.ADDITIONa mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent

Procedimiento

To a solution of 2-bromo-1-(4-fluorophenylmethyl)-1H-benzimidazole (0.244 g) in n-butanol (1 ml) was added 1-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane (1.00 g), and the mixture was refluxed for 2 hours. To the reaction mixture was added a saturated aqueous NaHCO3 solution (50 ml), and the mixture was extracted with methylene chloride (30 ml). The extract was washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on a silica gel column using a mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent to give a mixture (0.369 g) of 5-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane and 5-[2-[4-(2-n-butoxycarbonylethyl)phenyl]ethyl]-1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane.

Fuente