Hydrochloric Acid → N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(butylamino)propyl)propane-1,3-diamine) hydrochloride salt

Participants

Reaction Steps

To the crude N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(butylamino)propyl)propane-1,3-diamine) from step 2 was subjected to acidification with methanolic HCl (100 mL, 1.0M). The reaction mixture stirred at rt for 2 h. The reaction mixture was concentrated under reduced pressure and the solid was collected by vacuum filtration and washed with Et2O (50 mL) and hot MeOH (50 mL) to afford the desired product (1.24 g, 51%) as a white solid. 1H NMR (500 MHz, D2O) δ 7.83 (s, 2H), 7.71 (d, J=7.5 Hz, 2H), 7.55-7.52 (m, 3H), 7.49-7.45 (m, 1H), 4.35 (s, 4H), 3.26 (t, J=7.5 Hz, 4H), 3.21-3.16 (m, 8H), 3.14 (t, J=8.0 Hz, 4H), 3.05 (t, J=8.0 Hz, 4H), 2.21-2.10 (m, 8H), 1.65 (quint, J=7.0 Hz, 4H), 1.37 (sext, J=8.0 Hz, 4H), 0.91 (t, J=7.0 Hz, 6H). 13C NMR (125 MHz, D2O) δ 142.5, 138.9, 132.3, 130.3, 129.8, 129.5, 128.7, 127.3, 51.0, 47.8, 44.9, 44.5, 44.4, 27.7, 22.9, 22.9, 19.3, 13.0. LRMS [M+H]+553.5.

Provenance & Evidence