Pyridine, 4-[(3-methoxyphenyl)methyl]- → 4-[(3-Methoxyphenyl)methyl]piperidine

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Reaction Steps

A mixture of 4-(3-methoxybenzyl)pyridine (25 g, 126 mmole) and platinum oxide (2.4 g) in acetic acid (250 ml) was hydrogenated for 2 hr. The catalyst was removed and the solution concentrated in vacuo. The residue was dissolved in water and the solution basified with sodium hydroxide. The basic mixture was extracted with ether. The extracts were dried and concentrated in vacuo. The residue was vacuum distilled to give 4-(3-methoxy-benzyl)piperidine as an oil (22.6 g, 87.6% ). A sample of the hydrochloride was prepared in ether (mp: 146°-147° C.). Calc'd. for C13H19NO.HCl: C, 64.59%; H, 8.34%; N, 5.80%. Found: C, 64.38%; H, 8.34%; N, 5.66%.

Provenance & Evidence