Diisopropylethylamine → [3-(2-Benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amine

Participants

Reaction Conditions

Reaction Steps

1,1-di(p-anisyl)methylamine (2.06 g, 8.48 mmol) is added to a stirred solution of 2-benzyl-1-(3-bromo-propoxy)-4-chloro-benzene (2.40 g, 7.07 mmol) and diisopropylethylamine (1.85 mL, 10.6 mmol) in anhydrous 1,4-dioxane (10 mL) at ambient temperature under nitrogen. The mixture is heated at 95° C. for 24 hours. At ambient temperature, EtOAc (100 mL) and half-saturated aqueous NaHCO3 solution (60 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 5-12% EtOAc in hexane) to give 3.08 g (6.13 mmol, 87% yield) of the title compound as oil. ESIMS: m/z 502 [(M+H)+, 35Cl], 504 [(M+H)+, 37Cl].

Provenance & Evidence