1-Aminopiperidine → HCID 20232079, compound

Participants

Reaction Steps

n-Butyllithium (25 g/250 ml solution in hexane) (28.5 ml) was added dropwise to a stirred solution of N-aminopiperidine (4.12 g) in tetrahydrofurane (40 ml) at -78° C. and the stirring was continued for 2 hours at room temperature. A solution of 5-methyl-3-methylsulfonyl-6-phenyl-1,2,4-triazine (5 g) in tetrahydrofuran (100 ml) was added dropwise to the above obtained solution at -78° C. in 70 minutes with stirring and the stirring was continued for 30 minutes at the same temperature. The reaction mixture was washed with water and brine, and then extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated. The resulting residue was dissolved in chloroform and extracted with an aqueous solution of 6N-hydrochloric acid. The extract was made alkaline with an aqueous solution of potassium carbonate and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, and evaporated. Thus obtained crude product (3.82 g) was purified by chromatography on silica gel (100 g) using a mixture of benzene and ethyl acetate (2:1) as an eluent and recrystallized from diisopropyl ether to give crystals of 5-methyl-6-phenyl-3-piperidinoamino-1,2,4-triazine (2.25 g).

Provenance & Evidence