1-[2-(2-fluorophenoxy)ethyl]piperazine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a mixture of 3-(3,4,5-trimethoxyphenyl)propionic acid (0.36 g, 1.5 mmol), HOBt (0.24 g, 1.8 mmol), EDAC.HCl (0.34 g, 1.8 mmol) in DMF (4 mL) was added 1-[2-(2-fluoro-phenoxy)ethyl]piperazine (0.34 g, 1.5 mmol) and triethylamine (0.5 mL, 3.6 mmol). The mixture was then stirred at room temperature for a day, treated with water, and extracted with dichloromethane. The organic layer was washed with water and brine and then concentrated to dryness. The residue was dissolved in ethyl ether and was added with 2N HCl in ether (1 mL). The white solid was filtered and dried under vacuum to give the title compound (408 mg, 52%). extracted with dichloromethane The organic layer was washed with water and brine concentrated to dryness The residue was dissolved in ethyl ether was added with 2N HCl in ether (1 mL) The white solid was filtered dried under vacuum

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

Procedure: The above oil of 4-[2-(2-fluorophenoxy)ethyl]piperazine-1-carboxylic acid tert-butyl ester (4.0 g, 12 mmol) in dichloromethane (60 mL) was mixed with trifluoroacetic acid (10 mL) and was stirred at room temperature for 2 hours. The solvent was evaporated and the residue was treated with a saturated solution of NaHCO3. The aqueous solution was extracted with dichloromethane and the organic layer was concentrated to give 1-[2-(2-fluoro-phenoxy)ethyl]piperazine as a white solid (2.25 g, 84%). 1H NMR (400 MHz, DMSO-d6): δ 2.40 (b, 4H), 2.67 (m, 6H), 4.13 (t, 2H), 6.92 (m, 1H), 7.11 (t, 1H), 7.18 (m, 2H). The solvent was evaporated the residue was treated with a saturated solution of NaHCO3 The aqueous solution was extracted with dichloromethane the organic layer was concentrated