Nipecotic Acid → HCID 67338599, compound

Participants

Reaction Steps

To a suspension of cyanuric chloride (1.0 g, 4.1 mmol, 1.00 equiv) in 1:1 CH3CN:H2O at 0° C. was added NH2Me (2.0 M solution in THF, 2.0 mL, 4.1 mmol, 1.00 equiv). The pH of the reaction mixture was adjusted to a pH of 8-9 by treating with 1 N NaOH. The pH was maintained between 8 and 9 for 30 min (reaction progress was monitored by LCMS). Next 3-piperidinecarboxylic acid (0.53 g, 4.1 mmol, 1.00 equiv) was added to the reaction mixture. The pH of the reaction mixture was again maintained between 8 and 9 using 1 N NaOH. Next N-methylpiperazine (4.0 mL, 41 mmol, 10.0 equiv) was added to the reaction mixture and the mixture was heated at reflux overnight. The reaction mixture was concentrated, the crude product was dissolved in a mixture of methanol and water, and purified by HPLC to provide 0.9 g of the title compound. MS (ES+): m/e 336.2 [M+H]+.

Provenance & Evidence