2-(4-(2,3-Epoxypropoxy)phenyl)acetamide → N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-2-methyl-1H-benzimidazole-1-propanamine

Participants

Reaction Steps

A mixture of 4.16 grams of 2-methyl-1H-benzimidazole-1-propanamine and 4.56 grams of 1-[4-(2-amino-2-oxoethyl)phenoxy]-2,3-epoxypropane in 50 ml of 90% methanol was refluxed for 22 hours. The solvent was then evaporated to leave a thick oil which was chromatographed on a silica gel column using methanol. The fractions containing the desired product were determined by thin-layer chromatography and combined. The solvent was evaporated to leave a thick oily residue which solidified partially on standing. This was recrystallized from ethanol to give N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-2-methyl-1H-benzimidazole-1-propanamine melting at about 146°-149° C. This compound has the following structural formula: ##STR14##

Provenance & Evidence