1,1'-Carbonyldiimidazole → HCID 178432057, compound

Participants

Reaction Steps

In an atmosphere of argon, metallic sodium (446.6 mg, 0.019 g atom) was dissolved in anhydrous methanol (15.0 ml) at room temperature, and the solution was mixed with guanidine hydrochloride (1.89 g, 19.7 mmol) at 0° C. After 30 minutes of stirring at room temperature, the thus precipitated sodium chloride was removed by filtration using a glass filter and the resulting filtrate was evaporated under reduced pressure to obtain free guanidine. In an atmosphere of argon, 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylic acid (406.3 mg, 1.98 mmol) was suspended in THF (8.0 ml) and mixed with CDI (491.5 mg, 2.97 mmol) at room temperature. This was stirred at room temperature for 2 hours and then at 50° C. for 1 hour, mixed with the previously obtained guanidine THF suspension (6.0 ml) by its dropwise addition and then stirred at room temperature for 18 hours After evaporation of the solvent under reduced pressure, the thus obtained residue was mixed with waterandextractedwith ethyl acetate. The thus obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the thus formed crystals were washed with ether to obtain the title compound (192.5 mg, 39.5%) as white powder.

Provenance & Evidence