Triethylamine → HCID 178497018, compound

Participants

Reaction Steps

68.5 g methyl (6S)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate dihydrochloride, 81.8 g triethylamine and 63.3 g selenium dioxide were suspended in 1.1 l anhydrous 1,4-dioxane. The mixture was refluxed for 2 h. 26.3 g triethylamine were added and the mixture was allowed to cool down to room temperature and stirred overnight. The solvent was removed under reduced pressure and the residue was suspended in 300 ml methanol. 46.8 g triethylamine were added to adjust to pH 8-9. The resulting precipitate was filtered and washed with 70 ml methanol. The precipitate was treated with 500 ml N,N-dimethylformamide, stirred at 140° C. for 30 minutes and filtered hot. Upon cooling to room temperature, precipitation takes place. The precipitate was filtered, washed with 80 ml cold methanol and dried under vacuum to yield the title compound.

Provenance & Evidence