Sodium hydride → 2-Methyl-4-{[(piperidin-4-yl)oxy]methyl}quinoline

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Reaction Steps

To commercially available N-Boc-4-piperidinol (1.00 g, 5.0 mmol) in THF (50 mL) was added NaH (238 mg 60% oil dispersion) and after 25 min, 4-[(2-methyl-4-quinolinyl)methoxy]benzyl chloride (950 mg, 5.00 mmol). After 18 h, the reaction was quenched with water, the THF was removed by rotary evaporator, and the residue was extracted from water with 3×EtOAc. The combined organic extracts were dried over MgSO4, filtered, concentrated, and chromatographed on SiO2 using 40% EtOAc in hexane. Obtained 200 mg (11% yield) of desired product which was treated with TFA (2 mL) in DCM (5 mL) for 1 h. The solvents were removed by rotary evaporator and the product was obtained pure as a free base by extraction from aqueous NaHCO3 with EtOAc after drying over MgSO4, filtering, and concentrating in vacuo. MS found: (M+H)+=257.

Provenance & Evidence