Hydrochloric Acid → N-(5-(3-(N,N-Dimethylamino)propyloxy)-2-methylphenyl)tricyclo[3.3.1.13,7]decane-1-acetamide, hydrochloride

Participants

Reaction Conditions

Reaction Steps

Caesium carbonate (1.31 g) was added to a suspension of N-(3-hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide (0.473 g, Example 26) in acetonitrile (35 ml) and the mixture heated at 80° C. for 5 minutes. After cooling to room temperature solid N,N-dimethyl-3-chloropropylamine (0.274 g) was added and the reaction heated at reflux overnight. The reaction was concentrated under reduced pressure and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:ethanol:triethylamine (95:4:1) to give a yellow gumn. This was dissolved in methanol (10 ml) and treated with an excess of ethereal hydrogen chloride is (1M, 5 equivalents). The solution was concentrated under reduced pressure to give a gum that was stirred for 2 days in ether (20 ml) to give a solid which was isolated by filtration (0.588 g).

Provenance & Evidence