Réaction #87276

Équation de réaction

N1,N1′,N1″-([1,1′-biphenyl]-3,3′,5-triyltris(methylene))tris(N3-(3-(isobutylamino)propyl)propane-1,3-diamine)

N1,N1′,N1″-([1,1′-Biphenyl]-3,3,5-triyltris(methylene))tris(N3-(3-(isobutylamino)propyl)propane-1,3-diamine)

HCl

→

desired product

Rendement 52.0%

N1,N1′,N1″-([1,1′-Biphenyl]-3,3′,5-triyltris(methylene))tris(N3-(3-(isobutylamino)propyl)propane-1,3-diamine), hydrochloride salt

Rendement 52.0%

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture was concentrated under reduced pressure
2. 2
   Filtrationthe solid was collected by vacuum filtration
3. 3
   Lavagewashed with Et2O (50 mL) and hot MeOH (50 mL)

Mode opératoire

N1,N1′,N1″-([1,1′-biphenyl]-3,3′,5-triyltris(methylene))tris(N3-(3-(isobutylamino)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 (0.58 g, 52%) as a white solid. 1H NMR (500 MHz, D2O) δ ppm 7.91 (s, 1H), 7.85-7.82 (m, 3H), 7.65-7.56 (m, 3H), 4.42 (s, 4H), 4.39 (s, 2H), 3.29-3.16 (m, 24H), 2.93 (d, J=6.0 Hz, 6H), 2.20-2.13 (m, 12H), 2.07-2.00 (m, 3H), 0.99 (d, J=6.0 Hz, 18H). 13CNMR (125 MHz, D2O) δ ppm 141.6, 139.8, 132.2, 131.3, 130.4, 130.3, 129.7, 129.5, 128.6, 128.4, 54.8, 54.8, 51.1, 50.8, 44.7, 44.6, 44.2, 44.0, 25.5, 22.7, 22.5, 19.0. LRMS [M+2H+]2+376.8.

Source