Aminomethylation of α‐methylstyrene (1) leads to 1,2,3,6‐tetrahydro‐4‐phenylpyridine (3) as main product, together with a significant amount of a previously unknown by‐product. The N‐methyl, O‐acetyl‐N‐methyl, N, O‐diacetyl, N‐(4‐nitrobenzoyl), and (via N → O acyl‐migration) O‐(4‐nitrobenzoyl) derivatives of the by‐product were synthesized. By aromatization of the heteroring, 4‐phenyl‐3‐pyridinemethanol (8a) was obtained. According to these derivatives and their IR, 1H and 13C NMR spectra, the by‐product is 1,2,3,6‐tetrahydro‐4‐phenyl‐3‐pyridinemethanol (4a).
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