Piperazine → 1-(4-(Methylsulfonyl)phenyl)piperazine

Temperature

110 °C

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.

1. filtrationThe reaction mixture was filtered through a celite bed
2. washwashed with toluene
3. concentrationThe toluene was concentrated
4. extractionextracted with 1.5 (N) HCl solution three times
5. washThe combined aqueous layers were washed with diethyl ether
6. extractionextracted with ethyl acetate three times
7. washThe combined ethyl acetate layers were washed with water and saturated brine solution
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated
10. customchromatographed (9/1-CHCl3/MeOH)
11. customto afford the product

ORD record

ord-9deede0194644bb79af8f2c4f75b3765

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07449576B1