Reaction Steps
A concentrated solution of the amine 19 (0.253 g, 0.22 mmol) in ethyl acetate was added cooled to 0° C. A total of 5 mL of a freshly prepared saturated solution of HCl in ethyl acetate was added dropwise and the solution stirred for 1 h at room temperature during which time a white precipitate formed. The ethyl acetate was removed in vacuo and the residue co-evaporated with ethyl acetate and chloroform to give the product 26 as a white powder (0.215 g, 98%); 1H NMR (CD3OD) δ 7.13 (s, 1H, aryl), 7.04 (d, 1H, aryl), 6.98 (d, 1H, aryl), 5.33 (t, 4H, olefinic), 4.12 (m, 2H, benzylic), 4.03 (t, 2H, OCH2), 3.99 (t, 2H, OCH2), 3.08 (m, 10H, 5×CH2), 2.98 (t, 2H, CH2), 2.02 (m, 8H, CH2C═C), 1.89 (m, 16H, 8×CH2), 1.47 (m, 4H, 2×CH2), 1.42-1.19 (m, 40H, 20×CH2), 0.89 (t, 6H, CH3); 13C NMR (300 MHz, D2O) δ 149.74, 148.90, 129.62, 129.46, 123.92, 123.71, 69.36, 68.88, 51.12, 46.68, 38.99, 32.14, 29.97, 29.81, 29.60, 27.36, 26.53, 24.69, 24.22, 23.14, 23.06, 22.84, 14.05; HRMS (FAB): theory for C55H105N4O2 (M+1), 853.8238; found (M+1), 853.8264; Anal. (C55H109Cl4N4O2.0.6H2O): C, H, N.
