Sodium Iodide → HCID 69253831, compound

Participants

Reaction Steps

[3-(3-Bromo-propoxy)-phenyl]-acetic acid methyl ester (11.48 g, 0.04 mole) in acetonitrile (300 mL) was added dropwise over 45 minutes to a mixture of (R)-2-Phenyl-propylamine (1.3 eq., 7.04 g, 0.052 mole), sodium iodide (18.0 g, 0.12 mole), and potassium carbonate (16.6 g, 0.12 mole) in acetonitrile (2000 mL). The mixture was stirred five days. The reaction mixture was filtered and the filter cake washed with acetonitrile (500 mL). The acetonitrile was evaporated and the residue dissolved in methylene chloride and washed with water(2×), dried over magnesium sulfate, filtered and evaporated. The resulting residue was purified by silica gel chromatography (using 3% to 10% methanol/methylene chloride as elutant) to give the title compound (10.19 g, 75%). MS (ESI) 342 (M+H)+.

Provenance & Evidence