Cl[C:2]1[O:6][N:5]=[C:4]2[C:7]3[C:12]([CH2:13][CH2:14][C:3]=12)=[CH:11][CH:10]=[CH:9][CH:8]=3.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O.C(Cl)(Cl)Cl.C(Cl)Cl.CO>[N:15]1([C:2]2[O:6][N:5]=[C:4]3[C:7]4[C:12]([CH2:13][CH2:14][C:3]=23)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1A stirred mixture of 3-chloro-4,5-dihydronaphth[1,2-c]isoxazole (5.0 g, 24.4 mmol), piperazine(34.2 g, 397.7 mmol) and K2CO3 (6.73 g, 48.7 mmol) in 40 ml of N-methylpyrrolidinone under N2 was lowered into an oil bath preheated to 150° C. The mixture was heated while stirring under N2 for 45 minutes. At that time, TLC (CH2Cl2) showed no remaining starting material. The mixture was removed from the heating bath, allowed to cool to room temperature and extracted with Et2O. This organic phase was washed twice with H2O, dried over MgSO4, filtered and concentrated in vacuo to obtain a crude solid. The solid was collected, recrystallized from heptane/Et2O and dried in vacuo (0.1 mm) at 85° C. to provide pure product, mp of 97°-99° C., homogeneous by TLC [silica, 1:1 CH3OH:CH2Cl2, Rf=0.35]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =255, EI, 70 ev) were consistent with the structure. The yield was 3.372 g (13.22 mmol, 54.19%).
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