1-(2-Bromoethoxy)-4-methylbenzene → 4-(4-Methybenzyl)-1-(2-(4-methylphenoxy)ethyl)piperidine

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From a mixture of 4-(4-methylbenzyl)piperidine (1.14 g, 6.02 mmol), 2-(4-methylphenoxy)ethyl bromide (630 mg, 3.01 mmol) and KI (90 mg) in toluene (20 mL) was obtained 800 mg (85%) of the title compound as a yellow oil, 1H NMR (CDCl3): 1.26-1.38 (m, 2H), 1.45-1.53 (m, 1H), 1.61-1.66 (m, 2H), 1.99-2.07 (m, 2H), 2.277 (s, 3H), 2.317 (s, 3H), 2.494 (d, 2H, J=7), 2.761 (t, 2H, J=6), 2.95-2.99 (m, 2H), 4.067 (t, 2H, J=6), 6.792 (d, 2H, J=78), (d, 2H, J=8), 7.01-7.10 (m, 6H). The hydrocloride, mp 170-1° C.

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