1-Hydroxybenzotriazole → 1-Phenyl-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

Participants

Reaction Steps

DIPEA (66 mg, 0.088 mL, 0.51 mmol) was added to a stirred solution of 2-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (125 mg, 0.29 mmol) in DMF (1.5 mL). HOBT (27 mg, 0.20 mmol) and EDCI.HCl (39 mg, 0.20 mmol) were added at room temperature. After 2 minutes 1-phenyl-piperidine-4-carboxylic acid (35 mg, 0.17 mmol) was added. The resulting mixture was stirred at room temperature for four hours. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 25 mg (29% yield) of 1-phenyl-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity %: 87.42, HPLC Purity: 88.83%, 1H NMR (DMSO-d6): δ 7.8-7.5 (m, 3H), 7.4-7.3 (d, 1H), 7.3-7.2 (t, 1H), 7.0-6.9 (d, 1H), 6.8 (t, 1H), 6.6 (m, 1H), 4.2-3.7 (m, 4H), 3.8-3.6 (m, 4H), 3.5 (m, 2H), 3.4-3.3 (bt, 1H), 3.2 (m, 2H), 2.7 (m, 2H), 2.3 (m, 1H), 2.0-1.8 (m, 4H).

Provenance & Evidence