Hydrochloric Acid → 3-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(2-methoxyethyl)-3-methylbiphenyl-4-yl]propan-1-amine

Participants

Reaction Steps

To a solution of tert-butyl {3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2′-(2-methoxyethyl)-3-methylbiphenyl-4-yl]propyl}carbamate from step 4 (1 eq.) in CH2Cl2 (0.06M) at room temperature was added HCl 4M in dioxane (30 eq.). The reaction mixture was stirred for 3 h at room temperature and then concentrated to dryness. Purification by column chromatography on silica gel, eluting with CH2Cl2/MeOH(NH3 2M) 4%, afforded the title compound as a colorless oil. 1H NMR (400 MHz, acetone-d6): δ 7.46-7.20 (m, 6H); 7.22-7.12 (m, 2H); 7.07-6.97 (m, 3H); 6.81 (d, 2H); 4.39-4.32 (m, 4H); 3.60 (s, 3H); 3.55-3.45 (m, 2 H); 3.31-3.19 (m, 1H); 3.0-2.75 (m, 6H); 2.45 (t, 2H); 2.32 (s, 3H); 2.20 (s, 3H).

Provenance & Evidence