1,4-Bis(3-aminopropyl)piperazine → HCID 54371305, compound

Participants

Reaction Steps

Similar reaction of acridine-4-carboxylic acid imidazolide with 1,4-bis(3-aminopropyl)piperazine as above, and crystallization of the crude product from CH2Cl2 /EtOAc/iPr2O, gave N1,N4-bis[(acridine-4-carboxamido)propyl]piperazine (36) (91%). 1H NMR [(CD3)2SO] δ 11.39 (t, J=5.2 Hz, 2 H, 2×CONH), 9.33 (s, 2 H, H-9), 8.73 (d, J=7.0 Hz, 2 H, H-3), 8.38 (d, J=8.5 Hz, 2 H, ArH), 8.32-8.20 (m, 4 H, ArH), 7.97 (t, J=7.8 Hz, 2 H, ArH), 7.82-7.63 (m, 4 H, ArH), 3.57 (q, J=6.0 Hz, 4 H, 2×NHCH2), 2.6-2.3 t (m, 12 H, H-piperazine, 2×CH2CH2CH2N), 1.85 (quint, J=6.7 Hz, 4 H, CH2CH2CH2). Crystallization from MeOH/EtOAc/HCl gave the tetrahydrochloride salt, mp 248-253° C. Anal. (C38H38N6O2.4HCl) C, H, N, Cl.

Provenance & Evidence