tert-Butyl piperazine-1-carboxylate → HCID 58864146, compound

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The mixture of 4,7-dichloro-2-quinolinecarboxylic acid methyl ester (90.2 g, 379 mmol) and N-boc-piperazine (60.1 g, 387 mmol) in dry diisopropylethyl amine (300 mL) was kept at 140 degrees C. for 3 h. After the removal of diisopropylethyl amine in vacuo, ethyl ether was added to precipitate the product. The crude solid was collected by filtration and was purified by re-crystallization from EtOAc (500 mL) to afford 123 g (80%) of 7-chloro-4-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]-2-quinolinecarboxylic acid methyl ester as an off-white solid. 1H NMR (DMSO-d6): δ 1.42 (s, 18H), 3.18 (m, 4H), 3.61 (m, 4H), 3.92 (s, 3H), 7.47 (s, 1H), 7.63 (d, 1H), 8.04 (d, 1H), 8.1 (s, 1H).

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