tert-Butyl piperazine-1-carboxylate → HCID 58864146, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13](Cl)[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].[C:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(N(C(C)C)CC)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([N:27]2[CH2:26][CH2:25][N:24]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:29][CH2:28]2)[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).