1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide

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Reaction Steps

DIPEA (200 mg, 0.27 mL, 1.55 mmol) was added to a stirred solution of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid (60 mg, 0.32 mmol) in DMF (5 mL) followed by HOBt (47.6 mg, 0.35 mmol) and EDCI (153 mg, 0.8 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (107 mg, 0.35 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the precipitate formed was collected to afford 108 mg (76.6% Yield) of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 440.14, 95.71%. 1H NMR (300 MHz, DMSO-d6): δ 9.36 (s, 1H), 8.5 (t, 1H), 8.02 (d, 2H), 7.68 (m, 3H), 7.48 (d, 1H), 7.36-7.22 (m, 2H), 7.0 (t, 1H), 4.8 (m, 1H), 4.3 (d, 2H), 3.8 (t, 2H), 3.6 (s, 2H), 2.1 (d, 2H), 1.8 (d, 2H).

Provenance & Evidence