Triphenylphosphine → 4-(6-Morpholin-4-ylhexyl)-salicylamide

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A slurry of carsalam (6.13 g, 37.6 mmol), 4-(6-hydroxyhexyl)morpholine (7.0 g, 37.4 mmol), triphenylphosphine (9.97 g, 35.0 mmol), and tetrahydrofuran (40 mL) was treated with a solution of diisopropyl azodicarboxylate (7.40 mL, 7.60 g, 37.6 mmol) and tetrahydrofuran (10 mL), added dropwise over 15 minutes. The reaction mixture was stirred at 25° C. for 60 hours. The solution was treated with aqueous 2N NaOH (50 mL, 100 mmol) and warmed to 60° C. for 180 minutes. The cooled reaction mixture was concentrated to remove the tetrahydrofuran. The aqueous residue was washed with ethyl acetate (2×40 mL), and was acidified with 4% aqueous HCl to a pH of 0.84 (causing carbon dioxide gas to evolve). The pH of the aqueous phase was raised to 7.8 with 2N aqueous NaOH. Solid sodium bicarbonate was added. Extraction with ethyl acetate (8×40 mL), drying over sodium sulfate and concentration gave an oil which solidified upon standing. A total of 4.26 g of 4-(6-morpholin-4-ylhexyl)-salicylamide was isolated.

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