Sodium Iodide → 6-Butyl-8-[(1-{2-[(1,1-di methylethyl)sulfonyl]ethyl}-4-piperidinyl)oxy]quinoline, dihydrochloride salt

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-butyl-8-(4-piperidinyloxy)quinoline (for example, as prepared for Intermediate 4) (80 mg, 0.28 mmol), sodium iodide (37 mg, 0.25 mmol), sodium bicarbonate (168 mg, 2.0 mmol) and 2-chloroethyl 1,1-dimethylethyl sulfone (for example, as prepared for Intermediate 12) (208 mg, 1.1 mmol) in DMF (2 ml) was heated at 150° C. for 15 min in a Smith Creator™ microwave oven. The reaction mixture was applied to an SCX-2 cartridge (20 g) preconditioned with methanol and was eluted with methanol, followed by 10% aqueous 0.88 s.g. ammonia in methanol. The ammoniacal fractions were combined and concentrated in vacuo and the residue (118 mg) was purified by MDAP (×2). Appropriate fractions were combined and concentrated in vacuo to give the free base of the title compound (10 mg, 8%): This was diluted with methanol and treated with 1.25 M hydrogen chloride solution in methanol (0.05 ml) and the solution was evaporated in vacuo to give the title compound (12 mg): LCMS RT=2.73 min, ES+ve m/z 433 (M+H)+.

Provenance & Evidence