Diisopropylethylamine → HCID 23599501, compound

Participants

Reaction Steps

A mixture of (S)-N-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride (1.9 g), 5-bromothiophene-2-carboxylic acid (1.97 g), 1-hydroxybenzotriazole hydrate (1.28 g), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (3.06 g), and N,N-diisopropylethylamine (8.3 mL) in N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. The solution was evaporated, and the residue was partitioned between aqueous sodium hydroxide and chloroform. The chloroform layer was dried (Mg2SO4), filtered, and evaporated. The residue was purified by flash chromatography on silica gel and eluted with 5%-20% 3.5M methanolic ammonia/chloroform mixtures. Evaporation of solvent gave white solid (3 g); MS (ES+) 315, 317 (MH+).

Provenance & Evidence