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

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.

1. temperaturethe mixture was refluxed for 2 hours
2. extractionthe mixture was extracted with methylene chloride (30 ml)
3. washThe extract was washed with water
4. dry with materialdried over anhydrous MgSO4
5. customThe solvent was removed under reduced pressure
6. customthe residue was purified by medium pressure liquid column chromatography on a silica gel column
7. additiona mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent

ORD-Eintrag

ord-f99f3708ffbd4d07b06b88d0ac6b5bc9

Quelldatensatz

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05624948