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Reagents and conditions: i. dibromoalkane, tetra-n-butylammonium bromide (TBAB), MeCN, reflux, 20 h; ii. (a) 4-amino-1-benzylpiperidine, triethylamine (TEA), MeCN, reflux, 3 h (compound (cmp.) 1,2); (b) 1-(3-chlorobenzyl)piperidin-4-amine, TEA, MeCN, microwave (MW), 100 °C, 45 min. (cmp. 3); (c) benzylamine, K2CO3, MeCN, room temperature (RT), 48 h (cmp. 4,5); (d) 2-fluorobenzylamine, K2CO3, MeCN, RT, 48 h (cmp. 6).
