Acetic Acid → HCID 57874433, compound

Participants

Reaction Steps

37% Aqueous formaldehyde (29.22 mg, 0.97 mmol) solution was added to a stirred solution of 1-piperidin-4-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide hydrochloride (252 mg, 0.48 mmol) in a mixture of acetic acid (240 mg, 4.0 mmol) and H2O (2 mL) and stirring was continued at ambient temperature for 5 minutes. Zinc dust was added to the reaction mixture (94.1 mg, 1.44 mmol) and stirring was continued at ambient temperature for 1 hr. The reaction mixture was cooled, basified with aqueous ammonia solution and extracted with DCM. The organic layer was collected and dried over sodium sulfate and concentrated under reduced pressure to afford 110 mg (45.6% Yield) of 1-(1-methyl-piperidin-4-yl)-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 495.2. 1H NMR (300 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.3 (t, 1H), 7.5 (t, 1H), 7.3 (t, 3H), 4.8 (m, 1H), 4.5 (m, 1H), 4.2 (d, 2H), 3.9 (m, 1H), 3.7 (m, 1H), 3.4 (m, 2H), 2.9 (m, 2H), 2.2 (s, 3H), 2.1 (m, 6H), 1.95 (m, 2H).

Provenance & Evidence