Methanol → N1-[3-(2-benzyl-4-chloro-phenoxy)-propyl]-N1-[bis-(4-methoxy-phenyl)-methyl]-ethane-1,2-diamine

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Reaction Steps

LiAlH4 (6.88 mL, 1N in THF) is added dropwise to a stirred solution of {[3-(2-benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-acetonitrile (2.48 g, 4.58 mmol) in anhydrous THF (30 mL) at ambient temperature under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 20 hours. The mixture is cooled to 0° C. before it is treated dropwise with CH3OH (5 mL), then followed by the addition of Et2O (30 mL) and saturated Rochelle's salt solution (80 mL). The two-layered mixture is allowed to stir vigorously at ambient temperature under nitrogen for 1 hour. Another 60 mL Et2O is added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-4% 2N NH3/CH3OH in CH2Cl2) to give 1.92 g (3.52 mmol, 77% yield) of the title compound as oil. ESIMS: m/z 545 [(M+H)+, 35Cl]; 547 [(M+H)+, 37Cl].

Provenance & Evidence