Dicyclohexylcarbodiimide → 4-(4-Phenylbutyl)-N-(tetrahydropyran-2-yloxy)benzamide

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Reaction Steps

To a 0° C. solution of 4-(4-phenylbutyl)benzoic acid (700 mg, 2.8 mmol) in 40 ml of CH2Cl2 under argon was added tetrahydropyranyl hydroxylamine (H2N-OTHP) (654 mg, 2.0 eq.), 1-hydroxybenzotriazole (HOBt) (460 mg, 1.2 eq.), N,N'-dicyclohexylcarbodiimide (700 mg, 1.2 eq.) sequentially. After 0.5 hour at 0° the solution was allowed to warm to room temperature and stir under argon for 4 hours. The solution was filtered, concentrated in vacuo to yield a white solid which was chromatographed on LPS-1 silica gel eluting with 6:4 hexane/EtOAc. Product containing fractions were evaporated to give title compound, an oil 1.0 g (~100%).

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