4-Aminopyridine → HCID 14672910, compound

Participants

Reaction Steps

36 g of N-benzyloxycarbonyl glycine was dissolved in 400 ml of dimethylformamide and the solution was cooled to -8° C., to which 56.8 g of dicylohexylcarbodiimide dissolved in 50 ml of dimethylformamide was added while maintaining the temperature at -8° to -6° C. After stirring at -6° to -3° C. for 15 minutes, 17 g of 4-aminopyridine was added at -3° to -1° C. The reaction liquid was allowed to stand so as to rise its temperature to room temperature over 2 hours and stirred at room temperature overnight. Then, dicyclohexylurea was filtered off and dimethylformamide was distilled off under reduced pressure. The residue was purified through the chromatography on silica gel (silica gel 1 kg; chloroform-methanol (3%→6%) as the eluent) and recrystallized from methanol-ethyl acetate to obtain 35.2 g of 4-[(N-benzyloxycarbonyl glycyl)amino]pyridine having the melting point of 154° to 156° C. This was dissolved in 1 l of methanol and 2.3 g of palladium black was added thereto followed by subjecting to the catalytic hydrogenation at room temperature and under atmospheric pressure. After 5 hours, the catalyst was filtered off and the filtrate was concentrated to about 50 ml. 200 ml of ethyl acetate was added and again the resultant solution was concentrated to about 60 ml so as to obtain the precipitate, which was allowed to stand overnight and filtered to obtain the titled compound.

Provenance & Evidence