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

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Reaction Steps

To the crude N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(isobutylamino)propyl)propane-1,3-diamine) was added methanolic HCl (200 mL, 1.0M). The reaction mixture was stirred at rt for 1 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 as a white solid (3.07 g, 50%). 1H NMR (500 MHz, D2O) δ 7.87 (s, 2H), 7.75 (d, J=7.5, 2H), 7.59-7.48 (m, 4H), 4.39 (s, 4H), 3.26 (t, J=8.0 Hz, 4H), 3.21-3.12 (m, 12H), 2.92 (d, J=7.0 Hz, 4H), 2.21-2.10 (in, 8H), 2.01 (sept, J=7.0 Hz, 2H), 0.99 (d, J=7.0 Hz, 12H). 13C NMR (125 MHz, D2O) δ 142.8, 139.1, 132.4, 130.1, 129.8, 129.5, 128.7, 127.3, 55.1, 51.1, 44.9, 44.8, 44.4, 25.8, 22.8, 22.7, 19.2. LRMS [M+H]+553.5.

Provenance & Evidence