1-Iodo-2-(methoxymethyl)benzene → 4-n-Butyl-1-[4-(2-methoxymethylphenyl)-4-oxo-1-butyl]piperidine

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A 10 mL oven-dried flask was charged with Mg turnings (88 mg, 3.6 mmol) andweactivated under vacuum by the use of a heat-gun. Under inert atmosphere was added a suspension of 1-Iodo-2-methoxymethylbenzene (0.67 g, 2.7 mmol) in Et2O (4 mL) and the reaction mixture was allowed to reflux for 1 hours. A suspension of compound 8 (0.38 g, 1.8 mmol) in CH2Cl2 (4 mL) was added via a syringe and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) and stirred at rt for 2 hours followed by addition of NaOH (10 mL, 2 M). Addition of THF (15 mL) was followed by extraction with ethyl acetate (3×50 mL) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.51 g of crude 22. The crude product was subjected to CC [eluent:CH2Cl2:MeOH (99:1)] to give pure 22 (0.14 g, 23%); LC-MS [M+H]+ 331 (cald. 331.5).

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