Hydrochloric Acid → 3-(4-Aminomethyl-phenyl)-1-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-1-isopropyl-urea

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Reaction Steps

Through a solution of 3 g (6 mmol) (4-{3-[2-(3,4-Dichloro-phenyl)-2-hydroxy-ethyl]-3-isopropyl-ureido}-benzyl)-carbamic acid tert-butyl ester in 100 mL EtOAc was gently bubbled HCl gas for 15 min. The reaction mixture was then concentrated in vacuo and to the resulting residue was added 15 mL 1N LiOH solution. This was extracted 3×70 ml EtOAc and the combined extracts were washed with 10 ml brine, dried over Na2SO4, filtered and concentrated to give 2.2 g 3-(4-Aminomethyl-phenyl)-1-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-1-isopropyl-urea as a white solid which was used without further purification. 1H NMR(300 mHz, CD3OD) 7.71 (d, 1H, J=2 Hz); 7.53 (d, 1H, J=8 Hz); 7.37 (dd, 1H, J=8 and 2 Hz); 7.28 (m, 4H); 4.88(m, 1H); 4.34 (sept, 1H, J=7 Hz); 3.78 (s, 2H); 3.48(dd, 1H, J=9 and 16 Hz); 3.22 (m, 2H); 1.25 (d, 3H, J=7 Hz); 1.12 (d, 3H, J=7 Hz).

Provenance & Evidence