C(OC([N:8]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=O)=[CH:22][CH:21]=1)[CH2:9][CH2:10][NH:11][CH2:12][C:13](OCC)=[O:14])=O)(C)(C)C.Cl.O1CCOCC1.CC[N:38](C(C)C)C(C)C>>[N:26]1[O:28][N:38]=[C:24]2[CH:25]=[C:20]([CH2:19][CH2:18][N:8]3[CH2:9][CH2:10][NH:11][CH2:12][C:13]3=[O:14])[CH:21]=[CH:22][C:23]=12To a flask charged with ethyl [(2-{(tert-butoxycarbonyl)[2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate (500 mg, 1.3 mmol) and a stir bar was added 4N HCl in dioxane (3.2 mL, 13 mmol). When LC indicated the reaction was done, solvents were removed under reduced pressure. The resulting residue was dissolved in ethanol (20 mL), and Hunig's base (1.1 mL, 6.4 mmol) was added to the solution. The reaction was heated to 120° C. for 16 hours. LC showed formation of the desired product, which was purified by silica gel chromatography to provide 1-[2-(2,1,3-Benzoxadiazol-5-yl)ethyl]piperazin-2-one. LC-MS (IE, m/z): 247 [M+1]+.
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