Synthesis
General procedure for the synthesis of 4-(4-methyl-1-piperazinyl)benzylamine from 4-(4-methylpiperazin-1-yl)benzonitrile: Sodium borohydride (10 eq.) was added to a solution of 4-(4-methylpiperazin-1-yl)benzonitrile (1 eq.) and cobalt chloride hexahydrate (2.1 eq.). The reaction mixture was stirred for 5 hours and then filtered through a pad of diatomaceous earth. The organic phase was concentrated under reduced pressure. The yellow oil obtained was purified by rapid chromatography on silica gel (dichloromethane: methanol = 8:2) to afford the target compound 4-(4-methyl-1-piperazinyl)benzylamine as a white solid in 50% yield.1H NMR (400 MHz, methanol-d4): δ (ppm) 2.42 (s, 3H); 2.74 (t, J=8Hz, 4H); 3.17 (t. J=8Hz, 4H); 4.43 (s, 2H); 6.89 (d, J=8Hz, 2H); 7.18 (d, J=8Hz, 2H). Elemental analysis (C12H19N3) calculated values: C, 70.20; H, 9.33; N, 20.47; measured values: C, 70.10; H, 9.13; N, 20.27.
References
[1] Tetrahedron Letters, 2013, vol. 54, # 38, p. 5204 - 5206
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 26, p. 8261 - 8269
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5293 - 5305
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 741 - 745
