Reaktion #357943

Reaktionsgleichung

Piperazine

sodium t-butoxide

BINAP

1-Bromo-4-methanesulfonyl-benzene

→

1-(4-Methanesulfonyl-phenyl)-piperazine

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through a celite bed
2. 2
   Waschenwashed with toluene
3. 3
   EinengenThe toluene was concentrated
4. 4
   Extraktionextracted with 1.5 (N) HCl solution three times
5. 5
   WaschenThe combined aqueous layers were washed with diethyl ether
6. 6
   Extraktionextracted with ethyl acetate three times
7. 7
   WaschenThe combined ethyl acetate layers were washed with water and saturated brine solution
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   Einengenconcentrated
10. 10
    Sonstigechromatographed (9/1-CHCl3/MeOH)
11. 11
    Sonstigeto afford the product

Vorschrift

Piperazine (0.98 g, 11.5 mmol), Pd(II) acetate (0.017 g), sodium t-butoxide (0.37 g, 4.2 mmol) and BINAP (0.049 g) were stirred at room temperature in 10 mL dry toluene for 15 min. 1-Bromo-4-methanesulfonyl-benzene (0.9 g, 3.8 mmol) in 10 mL dry toluene was added into the reaction mixture. Then the reaction mixture was refluxed at 110° C. for 20 hrs. The reaction mixture was filtered through a celite bed and washed with toluene. The toluene was concentrated and the reaction mixture was taken in ethyl acetate and extracted with 1.5 (N) HCl solution three times. The combined aqueous layers were washed with diethyl ether. The aqueous layer was neutralized with 10% aqueous sodium hydroxide solution and then extracted with ethyl acetate three times. The combined ethyl acetate layers were washed with water and saturated brine solution, dried over anhydrous sodium sulfate, concentrated and chromatographed (9/1-CHCl3/MeOH) to afford the product.

Quelle