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

Temperature

110 °C

Piperazine (0.588 g, 6.84 mmol), Pd(II)acetate (0.027 g, 0.123 mmol), sodium t-butoxide (0.837 g, 10.06 mmol) and BINAP (0.154 g, 0.286 mmol) were stirred at room temperature in 10 mL dry toluene for 15 min. 4-trifluoromethoxy bromo benzene (1.5 g, 6.22 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, washed with toluene, concentrated, ethyl acetate added and then extracted with 1.5 (N) aqueous 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 and concentrated to afford the product.

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

ORD record

ord-b92944b3044c4c79b9d12b8a5b31e94b

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157464B2