Dichloromethane → 4-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)-piperidine hydrochloride

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Reaction Conditions

Reaction Steps

A mixture of N-Boc-piperidine-4-carboxylic acid (0.92 g, 4 mmol) and carbonyldiimidazole (0.65 g, 4 mmol) in 10 mL tetrahydrofuran was heated at reflux for 15 min. The mixture was added to the starting amine (Example 15, 0.6 g, 2 mmol) in 10 mL dimethylformamide and heated at 70° C. for 30 min. Triethylamine (0.4 g) was added and the mixture heated an additional 18 h. The solvent was evaporated and the yellow solid was washing with tetrahydrofuran, collected by filtration and dried to give 0.74 g. The solid was suspended in 50 mL methylene chloride, cooled in an icebath and treated with trifluoroacetic acid (1 g). After evaporating the solvent, the solid was washed with ether and acetone mixture and dried. Calc'd for C18H21N5O5.1.5HCl.H2O: C, 40.82; H, 4.57; N, 13.22; found-C, 40.35; H, 4.70; N, 12.91.

Provenance & Evidence