Methylamine → HCID 178482399, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4,6-trichloro-1,3,5-triazine (0.5 g, 2.0 mmol) in a solution of CH3CN:H2O (1:1, 20 mL) was cooled to 0° C. A 2 M solution of methylamine in THF (1 mL, 2.0 mmol) was added. The reaction mixture was adjusted to a pH of about 8-9 using 1 N NaOH. The pH was maintained at about 9-10 for 0.5 hour. LCMS analysis showed the complete consumption of the 2,4,6-trichloro-1,3,5-triazine. To this mixture was added cis-4-(methylamino)cyclohexanecarboxylic acid (0.32 g, 2.0 mmol). The reaction mixture was stirred at room temperature while the pH was maintained between 8 and 9. Next, 1-methylpiperazine (2 g, 20 mmol) was added and the mixture was heated to 50° C. overnight. The solvent was removed and the crude product was purified by HPLC to afford 0.32 g (0.09 mmol, 44% yield) of the desired product. MS (ES+): m/e 364.2 [M+H]+.

Provenance & Evidence