Reaktion #1454880

Reaktionsgleichung

DIAD

4-fluorophenol

2-(4-Methyl-piperazin-1-yl)-1-phenyl-ethanol

triphenylphosphine

→

product 13a

Ausbeute 76.0%

1-[2-(4-Fluoro-phenoxy)-2-phenyl-ethyl]-4-methyl-piperazine

Ausbeute 76.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONAfter complete dissolution
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   SonstigeIce-bath was removed
4. 4
   SonstigeThe product was purified
5. 5
   Wascheneluting pure ethyl acetate
6. 6
   Sonstigeto recover any starting materials
7. 7
   TemperaturPolarity of the solvent was then increased

Vorschrift

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).

Quelle