1H-imidazole-2-carbaldehyde → HCID 67103762, compound

Participants

Reaction Steps

Commercially available methyl 4-aminomethyl-benzoate hydrochloride was subjected to desalting, thereby obtaining a free compound. The resultant free compound (1.04 g) was dissolved in methanol (15.0 ml) and added with 2-imidazole carboxaldehyde (0.529 g), and the whole was stirred at room temperature for 14 hours. After having been cooled to 0° C., the solution was added with sodium borohydride (0.249 g) and the whole was stirred at 0° C. for 30 minutes and then at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The extract was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off, thereby obtaining a crude product (1.47 g) of 4-[[(1H-imidazol-2-ylmethyl)-amino]-methyl]-benzoic acid methyl ester. The resultant crude product (1.47 g) was dissolved in methanol (15.0 ml) and added with 1-methyl-2-imidazole carboxaldehyde (0.844 g) and the whole was stirred at room temperature for 1 hour. After having been cooled to 0° C., the solution was added with sodium triacetoxyborohydride (2.18 g) and then the whole was stirred at room temperature for 22 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution. After extraction with chloroform, the organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.44 g) as white foam.

Provenance & Evidence