1-(2-BROMOETHOXY)-2-FLUOROBENZENE

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-cyano-N-methyl-N-[2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethyl]-benzenesulfonamide dihydrochloride (0.127 g, 0.30 mmol, prep I above), 1-(2-bromo-ethoxy)-2-fluoro-benzene (0.069 g, 0.315 mmol;) and potassium carbonate (0.145 g, 1.05 mmol) was added acetonitrile (4 mL) and water (0.1 mL). The mixture was heated by microwave irradiation (10 minutes, 160° C.) and was then filtered and evaporated. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 85 mg (58.0%) of the title compound. was then filtered evaporated The crude product was purified by chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of piperazine-1-carboxylic acid tert-butyl ester (2.79 g, 15 mmol) and 1-(2-bromoethoxy)-2-fluoro-benzene (3.28 g, 15 mmol) in DMF (6 mL) was added cesium carbonate (Cs2CO3, 9.75 g, 30 mmol). The mixture was stirred at room temperature for a day and then treated with water. The aqueous solution was extracted with ethyl acetate and the extract was washed with water and brine. The organic layer was concentrated and the residue was dried under the vacuum to yield the title compound quantitatively as an oil (5.1 g). 1H NMR (400 MHz, DMSO-d6): δ 1.39 (s, 9H), 2.44 (t, 4H), 2.73 (t, 2H), 3.29 (t, 4H), 4.45 (t, 2H), 6.93 (m, 1H), 7.11 (t, 1H), 7.18 (m, 2H). The aqueous solution was extracted with ethyl acetate the extract was washed with water and brine The organic layer was concentrated the residue was dried under the vacuum