C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][N:15]=2)[CH2:9]1)C1C=CC=CC=1.[Cl:25]C(OCCCl)=O>ClCCCl>[ClH:25].[C:19]1([C:17]2[O:16][N:15]=[C:14]([CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)[N:18]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1To a stirred solution of 4-benzyl-2-(5-phenyl-1,2,4-oxadiazol-3-yl)morpholine (intermediate 27, 900 mg, 2.80 mmol) in 1,2-dichloroethane (2.0 ml) was added chloroethyl chloroformate (0.46 ml, 4.20 mmol), and the reaction mixture was stirred at 70° C. for 4 hours. The reaction mixture was concentrated in vacuo. After removal of the solvent, the residue was dissolved in methanol (2.0 ml), and the solution was stirred under reflux for one hour. When the reaction was complete (checked by thin layer chromatography), the reaction mixture was concentrated in vacuo. The resulting 2-(5-phenyl-[1,2,4]oxadiazol-3-yl)-morpholine hydrochloride (intermediate 28) was used for next reaction without further purification.
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