1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 9H-fluorene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

Beteiligte Stoffe

Reaktionsschritte

DIPEA (184 mg, 0.24 mL, 1.42 mmol) was added to a stirred solution of 9H-fluorene-2-carboxylic acid (100 mg, 0.47 mmol) in DMF (2 mL). HOBT (64 mg, 0.47 mmol) and EDCI (109 mg, 0.57 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (167 mg, 0.47 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitated. The solid obtained was recrystallized from a mixture of ethyl acetate and hexane afford 105 mg (43.4%) of 9H-fluorene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 98.25%. 1H NMR (DMSO-d6): δ 8.6 (m, 1H), 8.1 (s, 1H), 8.0-7.4 (m, 10H), 4.2 (bs, 2H), 4.0 (s, 2H), 3.8-3.4 (m, 6H), 3.2 (b, 2H).

Herkunft & Nachweise