2-(4-methylpiperazin-1-yl)-1-phenylethanol

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: 2-(4-Methyl-piperazin-1-yl)-1-phenyl-ethanol (38) (2.0 g, 9.09 mmol) was dissolved in 50 mL of THF. 4-trifluoromethyl phenol was added to the solution and then triphenylphosphine. After complete dissolution, the mixture was cooled to 0° C. and after 10 minutes DIAD was added dropwise. Ice-bath was removed and the reaction mixture was stirred at room temperature for 48 hours. The product was purified using flash chromatography, using pure ethyl acetate. The product 14a (2.78 g, 7.64 mmol, 84%) was afforded as a yellow oil. H-NMR (CDCl3): δ 7.39 (2H, d, J=8.62), 7.36 (5H, m), 6.91 (2H, d, J=8.58), 5.38 (1H, dd, J=3.11, 3.10 Hz), 3.03 (1H, dd, J=8.39, 8.38), 2.71 (1H, dd, J=3.14, 3.14), 2.63 (4H, b), 2.44 (4H, b), 2.27 (3H, s). After complete dissolution was added dropwise Ice-bath was removed The product was purified

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

Procedure: 2-(4-Methyl-piperazin-1-yl)-1-phenyl-ethanol (38) (2.0 g, 9.09 mmol) was dissolved in 50 mL of THF. 4-fluorophenol was added to the solution and then triphenylphosphine. After complete dissolution, the mixture was cooled to 0° C. and after 10 minutes DIAD was added dropwise. Ice-bath was removed and the reaction mixture was stirred at room temperature for 48 hours. The product was purified using flash chromatography, eluting pure ethyl acetate to recover any starting materials. Polarity of the solvent was then increased using 30:70 methanol/ethyl acetate. The product 13a (2.18 g, 6.94 mmol, 76%) was afforded as a orange-brown oil. 1H-NMR (CDCl3): δ 7.33 (5H, m), 6.80 (4H, m), 5.21 (1H, dd, J=3.08, 3.07 Hz), 3.00 (1H, dd, J=8.49, 8.48), 2.67 (5H, b), 2.45 (4H, b), 2.27 (3H, s). After complete dissolution was added dropwise Ice-bath was removed The product was purified eluting pure ethyl acetate to recover any starting materials Polarity of the solvent was then increased