반응 #69570

반응 방정식

(2S)-2-methylpiperazine

Sodium hydroxide

4-(trifluoromethyl)benzenesulfonyl chloride

→

title compound

수율 64.9%

(3S)-3-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

수율 64.9%

용매

tetrahydrofuran

DCM

water

반응 조건

후처리

1. 1
   workup.STIRRINGmixture stirred for 10 min
2. 2
   workup.STIRRINGstirred for 5 min
3. 3
   기타The phases were separated
4. 4
   추출the aqueous layer was extracted with DCM (1000 ml)
5. 5
   농축the organic phases concentrated under reduced pressure
6. 6
   세척washed with DCM in order
7. 7
   추출to extracted impurities
8. 8
   추출extracted with DCM (3×500 ml)
9. 9
   건조the combined organic phases dried over Na2SO4 before the solvent
10. 10
    기타was removed under reduced pressure

실험 절차

(2S)-2-methylpiperazine (15 g, 150 mmol) was dissolved in tetrahydrofuran (300 mL) and the solution was cooled down to 0° C. Sodium hydroxide (150 mL, 449 mmol) was added, then 4-(trifluoromethyl)benzenesulfonyl chloride (40 g, 164 mmol) (dissolved in 200 ml THF) was added dropwise and the resulting mixture was stirred for 1 h. Further 4-(trifluoromethyl)benzenesulfonyl chloride (0.06 eq, 2.2 g) was added and mixture stirred for 10 min. The mixture was diluted with DCM (500 ml) and water (500 ml) and stirred for 5 min. The phases were separated, the aqueous layer was extracted with DCM (1000 ml) and the organic phases concentrated under reduced pressure. The residue was taken-up with 1 M HCl (500 ml) and washed with DCM in order to extracted impurities. The aqueous phase was basified to pH=9 with NaOH 3M, extracted with DCM (3×500 ml) and the combined organic phases dried over Na2SO4 before the solvent was removed under reduced pressure to give the title compound (30 g).

출처