Water → HCID 22645392, compound

Participants

Reaction Steps

To a solution of 1-hexyl-3,4-dimethyl-4-(3-trifluoromethanesulfonyloxyphenyl)piperidine (Preparation 1, 350 mg, 0.83 mmol) in tetrahydrofuran (12 mL) was added diisopropylamine (4 mL) and trimethylsilylethyne (4.5 g, 46 mmol) and the mixture was de-oxygenated by evacuating and flushing with nitrogen five times. Copper(I) iodide (6.2 mg 0.033 mmol), and then catalytic quantities of palladium(II) acetate and 1,1 ′-bis(diphenylphosphino)ferrocene were added. The reaction mixture was heated to reflux under nitrogen for 8 hours, before being allowed to cool to room temperature. Water (10 mL) and dichloromethane (10 mL) were added, the phases separated and the aqueous layer further extracted with dichloromethane (2×10 mL). The combined organics were then dried (Na2SO4) and the solvent removed in vacuo. The residual brown oil was purified by column chromatography on silica gel (25 g) eluted with a gradient of ethyl acetate:hexane:0.880 ammonia (20:79:1 to 50:49:1) to give the title compound as an oil (150 mg).

Provenance & Evidence