1-Naphthoic acid → HCID 18933042, compound

Participants

Reaction Steps

Homopiperazine (0.60 g, 6.0 mmol), naphthalene carboxylic acid (0.51 g, 3.0 mmol), 1-hydroxybenzotriazole (0.45 g, 3 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl) (0.63 g, 3.3 mmol) were added to dry, degassed dimethylformamide (7 mL). The pH of the reaction was adjusted to 7 with triethylamine, and the reaction stirred overnight. The dimethylformamide was distilled in vacuo, and the residue partitioned between ethyl acetate and water. The organic phase was washed with water and saturated sodium chloride solution, and dried over magnesium sulfate. The crude product was chromatographed on silica gel using chloroform/methanol as eluant and the title compound was isolated (0.100 g). NMR (CDCl3, 300 MHz) d 7.88 (2H, m), 7.50 (3H, m), 7.27 (1H, m), 4.08 (1H, m), 3.81 (1H, m), 3.28 (2H, m), 3.18 (1H, m), 3.00 (1H, m), 2.92 (1H, t, J=7 Hz), 2.72 (1H, t, J=7 Hz), 2.20 (1H, m), 1.58 (1H, m).

Provenance & Evidence