Phenylacetylene → HCID 69606755, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1-(methylsulfonyl)-4-(4-bromophenyl)piperazine (5.77 g, 18.1 mmol), phenyl acetylene (3.97 mL, 36.1 mmol), Copper (I) iodide (38 mg, 0.2 mmol) and triphenylphosphine (95 mg, 0.36 mmol) in piperidine (72 mL) at 20° C. was added dichlorobis(triphenylphosphine)palladium(II) (38 mg, 54 mmol). The reaction was warmed to 105° C. and stirred for 14 hours under an inert atmosphere. Volatiles were removed in vacuo, and the solid residue was dissolved in CH2Cl2 (200 mL) and washed with aqueous hydrochloric acid (2M) to pH 2. The layers were then separated and the organic extract dried, (sat. Brine and MgSO4), filtered and evaporated to dryness in vacuo. The residue was triturated in CH2Cl2, and filtered to give 1-(methylsulfonyl)-4-[4-(phenylethynyl)phenyl]piperazine as a flaky white solid (1.99 g, 5.86 mmol, 32%).

Provenance & Evidence