Scheme 1.
Mechanochemical synthesis of final compounds 6–19. Reagents and conditions: (i) vbm 30 Hz, ϕball = 1.5 cm, total mass of reagents = 500 mg, 35 mL PTFE jar, alkylating agent (1 eq) Boc-protected alicyclic diamine (1.2 eq), K2CO3 (3 eq), KI (0.5 eq), 210 min; (ii) HClgas, 2 h; (iii) vbm 30 Hz, ϕball = 1.5 cm, total mass of reagents = 125 mg, 10 mL PTFE jar, primary amine (1 eq), arylsulfonyl chloride (1 eq), K2CO3 (2 eq), 1–10 min.