Hydrochloric Acid → 6-Pentyl-8-(4-piperidinyloxy)quinoline

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Reaction Steps

1,1-Dimethylethyl 4-[(6-pentyl-8-quinolinyl)oxy]-1-piperidinecarboxylate (for example, as prepared for Intermediate 7) (2.20 g, 5.52 mmol) was dissolved in dioxane (10 ml) and the solution was treated with a solution of hydrogen chloride in dioxane (4M, 12.5 ml). The mixture was stirred under nitrogen overnight at room temperature, and then concentrated in vacuo. The residue was applied to a SCX-2 ion exchange cartridge (70 g) which had been preconditioned with methanol. The cartridge was washed with methanol, and then eluted with 10% aqueous 0.88 s.g. ammonia in methanol. The relevant basic fractions were concentrated in vacuo to give the title compound (1.88 g); LCMS RT=2.70 min, ES+ve m/z 299 [M+H]+.

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