Phenol → 3-Dimethylaminomethyl-4-(3-hydroxy-phenyl)-1-(1-phenyl-cyclohexyl)-piperidin-4-ol Dihydrochloride

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Reaction Steps

The synthesis instructions are described analogously to Example 6, except for the last step. The methyl ether was then cleaved into the phenol. To that end, 0.5 g (1.2 mmol.) of the free base of compound (6) was dissolved in 5 ml of toluene, and 10 ml of dibutylaluminium hydride solution (1.5 M in toluene) were added at 0° C. and under a nitrogen atmosphere. After 12 hours' stirring, the batch was hydrolysed with 5 ml of ethyl acetate and 5 ml of ethanol, the solvent was removed in vacuo, the residue was dissolved in methyl ethyl ketone, and 1.0 ml of trimethylsilyl chloride was added thereto. The yield of (11) was 71 mg (0.15 mmol., 12%). The compound melted between 245 and 248° C.

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