Piperazine → 1-Benzyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

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Reaction Steps

A solution of 1-benzyl-4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (8) (530 mg, 1.79 mmol) in dichloromethane was added slowly to a stirred solution of piperazine (463 mg, 5.37 mmol) in dichloromethane at room temperature. The solution was further stirred overnight at room temperature and diluted by dichloromethane. The solution was subsequently washed with saturated NaHCO3 solution, water and brine, then dried over Na2SO4 and evaporated to yield 610 mg (98%) of 1-benzyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (9) as white solids. MP: 211° C.; 1H-NMR (DMSO-d6): δ 2.93 (m, 4H), 3.57 (m, 4H), 5.53 (s, 2H), 7.20-7.27 (m, 5H), 7.34 (dd, J=4.8, 8.0 Hz, 1H), 8.26 (dd, J=1.6, 8.0 Hz, 1H), 8.65 (dd, J=1.6, 8.0 Hz, 1H); EIMS: 296 (M+1). EIMS: 346 (M+1).

Provenance & Evidence