Triethylamine → HCID 9811366, compound

Participants

Reaction Steps

While 39.11 g (0.1792 mol) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 21.7 g (0.188 mol) of N-hydroxysuccinimide were stirred together in 500 ml of acetonitrile, 36.1 g (0.188 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added, and the mixture was stirred at room temperature overnight. To this reaction mixture was added 30.0 ml (0.215 mol) of triethylamine and, then, a solution of 39.1 g (0.179 mol) of 4-amino-1-(3-phenylpropan-1-yl)piperidine in acetonitrile (100 ml)-chloroform (50 ml) was added. The mixture was stirred at room temperature for 1 hour and the resulting orange-colored precipitate was recovered by filtration and rinsed with acetonitrile (yield 55.75 g). This crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 4/1˜1/1) and recrystallization from chloroform-ethanol to provide the title compound.

Provenance & Evidence