1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874494, compound

Participants

Reaction Steps

DIPEA (137 mg, 1.0 mmol) was added to a stirred solution of to a stirred solution of 9H-carbazole-3-carboxylic acid (50 mg, 0.23 mmol) in DMF (4 mL) followed by HOBt (35 mg, 0.26 mmol) and EDCI (116 mg, 0.59 mmol). After 2 minutes, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (88 mg, 0.26 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water and the precipitate was filtered. The solid obtained was purified by recrystallisation from a mixture of 10% ethyl acetate in hexane and 50% MeOH in H2O to afford 81 mg (69.23% Yield) of 9H-carbazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 496, 91.03%. 1H NMR (300 MHz, DMSO-d6): δ 11.6 (s, 1H), 8.8 (s, 1H), 8.6 (t, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.6 (d, 2H), 7.46 (t, 1H), 7.36 (t, 2H), 7.24 (t, 1H), 4.9 (b, 1H), 4.3 (d, 3H), 4.0 (d, 2H), 3.5 (d, 2H), 2.1 (t, 2H), 1.7 (d, 2H).

Provenance & Evidence