Sodium Iodide → 1-(3-{4-[4-Methyl-5-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]phenoxy}propyl)piperidine

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Reaction Steps

A suspension of 1-({2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetyl)piperidine i104 (0.18 g, 0.51 mmol, 1 eq), potassium carbonate (0.14 g, 1.02 mmol, 2 eq) and sodium iodide (16 mg, 0.03 mmol, 0.2 eq) in acetonitrile (3 ml) is stirred at 80° C. for 20 minutes before addition of piperidine (0.15 ml, 0.51 mmol, 1.03 eq). The mixture is then stirred at reflux overnight, concentrated under vacuum and the residue is taken up in ethyl acetate (50 ml). The organic layer is washed with water (3×25 ml), brine, dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure to obtain an orange solid. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 90:10:1) affords 150 mg of 1-(3-{4-[4-methyl-5-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]phenoxy}propyl)piperidine 127.

Provenance & Evidence