p-Toluenesulfonic acid monohydrate → HCID 12017138, compound

Participants

Reaction Steps

The crude 3-{2-[3-(tetrahydro-pyran-2-yloxy)-propyl]-benzimidazol-1-yl }-propionitrile was stirred in 250 mL of methanol with sufficient p-toluenesulfonic acid monohydrate to make the solution acidic (pH=1-2). After stirring overnight, the solution was concentrated under reduced pressure, made basic (pH=8) with 1N sodium hydroxide and extracted into 8×50 mL of ethyl acetate. The aqueous layer was saturated with NaCl to aid in extraction of the product. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography using a gradient of ethyl acetate then 10% methanol in ethyl acetate followed by trituration with ether-hexane gave 4.8 g of 3-[2-(3-hydroxy-propyl)-benzimidazol-1-yl]-propionitrile as a solid.

Provenance & Evidence