Bis(3-aminopropyl)amine → HCID 23299929, compound

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Reaction Steps

Similar reaction of acridine-4-carboxylic acid imidazolide with N,N-bis(3-aminopropyl)amine as above, followed by purification of the product by chromatography on alumina-90, eluting with CH2Cl2 /MeOH (20:1), gave bis[3-(acridine-4-carboxamido)propyl]amine (35) (80%) as an oil. 1H NMR [(CD3)2SO] δ 11.40 (t, J=5.4 Hz, 2 H, 2×CONH), 9.19 (s, 2 H, H-9), 8.71 (d, J=7.1 Hz, 2 H, H-3), 8.32 (d, J=8.5 Hz, 2 H, ArH), 8.18-8.00 (m, 4 H, ArH), 7.83-7.62 (m, 4 H, ArH), 7.51 (t, J=7.5 Hz, 2H, ArH), 3.64 (q, J=6.0 Hz, 4H, 2×CONHCH2) 2.86 (t, J=6.7 Hz, 4H, CH2NHCH2) 1.92 (quint, J=6.5 Hz, 4 H, 2×CH2CH2CH2). Crystallization from MeOH/EtOAc/HCl gave the trihydrochloride salt, mp 171-173° C. Anal. (C34H31N5O2.2HCl.2H2O) C, H, N, Cl.

Provenance & Evidence