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

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-butyl-8-(4-piperidinyloxy)quinoline (for example, as prepared for Intermediate 4) (65 mg, 0.23 mmol), sodium iodide (47 mg, 0.3 mmol), sodium bicarbonate (190 mg, 2.2 mmol) and 4-bromobutyl 1,1-dimethylethyl sulfone (for example, as prepared for Intermediate 22) (94 mg) in DMF (2 ml) was heated in a Smith Creator™ microwave oven at 150° C. for 20 min. The reaction mixture was applied to an SCX-2 cartridge (10 g), preconditioned with methanol, and 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 (100 mg) was purified by MDAP to give the title compound (58 mg, 46%): LCMS RT=2.65 min, ES+ve m/z 461 (M+H)+.

Provenance & Evidence