Bromoacetonitrile → {[3-(2-Benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-acetonitrile

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Reaction Conditions

Reaction Steps

Bromoacetonitrile (0.575 mL, 8.25 mmol) is added to a stirred solution of [3-(2-benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amine (2.76 g, 5.50 mmol) and diisopropylethylamine (1.44 mL, 8.25 mmol) in anhydrous 1,4-dioxane (20 mL) at ambient temperature under nitrogen. The mixture is heated at 90° C. for 4 hours. At ambient temperature, EtOAc (100 mL) and half-saturated aqueous NaHCO3 solution (100 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 5-16% EtOAc in hexane) to give 2.88 g (5.32 mmol, 97% yield) of the title compound as oil. ESIMS: m/z 541 [(M+H)+, 35Cl], 543 [(M+H)+, 37Cl]. Analysis for C33H33ClN2O3: calcd: C, 73.25; H, 6.15; N, 5.18; found: C, 73.05; H, 6.28; N, 5.02.

Provenance & Evidence