p-Toluenesulfonic acid → 4-(4-(Benzyl(methyl)amino)cyclohex-1-enyl)-N,N-dimethylpyridin-2-amine

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Reaction Steps

A mixture of 4-(benzyl(methyl)amino)-1-(2-(dimethylamino)pyridin-4-yl)cyclohexanol (300 mg, 0.88 mmol, 1.0 eq.) and PTSA (1.1 g, 5.31 mmol, 6.0 eq.) in toluene (10 ml) was refluxed for 16 hours. After monitoring by TLC, the mixture was concentrated and the residue was taken up in DCM and washed with sat. NaHCO3 solution (3×30 ml), water (30 ml) and sat. NaCl solution (30 ml). The org. phase was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 3% MeOH in DCM). Yield: 57% (160 mg, 0.50 mmol)

Provenance & Evidence