Sodium hydride → HCID 11617608, compound

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Reaction Steps

To a suspention of NaH (100 mmol, 55-65% in oil) in dry dioxane (140 mL) was added 3-dimethylamino-1-propanol (11.90 mL, 100 mmol). The mixture was stirred 1 h at room temperature. A solution of 4-fluoro-N-(4-chlorophenyl)benzenesulfonamide (9.53 g, 33.35 mmol, preparation described in example 66) in dry dioxane (35 mL) was added. The resulting mixture was heated 24 h at 100° C. Solvents were evaporated. NH4Cl saturated solution in water (75 mL) was added and the desired product was extracted with three portions of ethyl acetate (3×100 mL). Combined organic phases were dried over magnesium sulfate before filtering and removal of solvent. The desired product, e.g. N-(4-chlorophenyl)-4-[3-(dimethylamino)propoxy]benzenesulfonamide was obtained as a colorless oil, in 96% purity by HPLC (MaxPlot detection between 230 and 400 nm). This intermediate was used in the next step without further purification.

Provenance & Evidence