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Reagents and conditions: (a) hydrazine hydrate, Pd/C (10%), EtOH, 81%; (b) 1-(benzyloxy)-4-(2-bromoethyl)benzene, K2CO3, DMF, 70 °C, 15%; (c) H2, Pd/C (10%), MeOH, 48%; (d) N-chloroethylpiperidine, K2CO3, DMF, 70 °C, 8%; (e) bromoacetylbromide, NEt3, DCM, 75%; (f) for F1–3, secondary amine, K2CO3, acetone, 48–90%; (g) for F4, i) boc-piperazine, K2CO3, acetone, ii) 6 M HCl, MeOH, 72%.
