Triethylamine → HCID 69837392, compound

Participants

Reaction Steps

A solution of 2-chloroquinoline-4-carboxylic acid dimethylamide (512 mg, 2.18 mmol), tert-butyl N-(3-aminopropyl)carbamate (571 μl, 3.27 mmol), and triethylamine (608 μl, 4.36 mmol) in absolute ethanol (35 ml) was heated at reflux for 7 days. The reaction was then allowed to cool to ambient temperature and was evaporated under reduced pressure to give a yellow oil. The residue was purified by column chromatography (ethyl acetate), dissolved in methylene chloride (10 mL), and treated with 4 N hydrogen chloride in dioxane (3 mL). The reaction was maintained at ambient temperature for 24 hours. Evaporation under reduced pressure gave 2-(3-aminopropylamino)quinoline-4-carboxylic acid dimethylamide dihydrochloride (218 mg, 30%) as a pale yellow solid. [M+H]+ 273.

Provenance & Evidence