Benzhydrol → 4-((Diphenylmethoxy)methyl)piperidine

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Reaction Steps

To a round bottom flask, benzhydrol (1.84 g, 10 mmol, 1.0 eq.), piperidin-4-yl-methanol (1.15 g, 10 mmol, 1.0 eq.), and p-toluenesulfonic acid monohydrate (2.09 g, 1.1 eq.) were suspended in toluene (400 ml). The mixture was refluxed with a Dean-Stark condenser for 3-4 hours. After cooling to room temperature, the solution was washed with 5% NaOH solution (2×20 ml), then with water (2×20 ml). The solution was then dried over anhydrous Na2SO4. The solvent was then removed under vacuum. The crude product 4-(1,1-diphenyl-methoxymethyl)-piperidine was obtained (2.33 g, 82.8% yield). ESMS 268.1 (M+1), 290.1 (M+23).

Provenance & Evidence