1-[2-(4-Benzyloxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride → 1-[2-(4-Hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride

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Reaction Steps

A mixture of 1-[2-(4-benzyloxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride (250 mg, 0.55 mmol) in 25 mL of ethanol with 60 mg of 20% Pd(OH)2 was hydrogenated at 30 psi of hydrogen to give 140 mg (88%) of the title compound, mp 198-200° C. 1H NMR (CD3OD) 1.6 (m, 2 H), 1.881-1.923 (m, 3 H), 2.288 (s, 3 H), 2.572 (d, J=6.6 Hz, 2 H), 3.06 (m, 2 H), 3.473 (m, 2 H), 3.61 (m, 2 H), 4.243 (t, J=5.1 Hz, 2 H), 6.709 (dd, J1 =2.4 Hz, J2 =6.6 Hz, 2 H), 6.830 (dd, J1 =2.4 Hz, J2 =6.6 Hz, 2 H), 7.703 (m, 4 H). Anal. Calcd for C21H28ClNO2.0.5H2O: C, 68.00; H, 7.88; N, 3.78. Found: C, 68.14; H, 7.65; N. 3.72.

Provenance & Evidence