تفاعل #71642

معادلة التفاعل

(2S)-2-methylpiperazine

Sodium hydroxide

4-(trifluoromethyl)benzenesulfonyl chloride

→

title compound

المردود 64.9%

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

المردود 64.9%

المذيبات

tetrahydrofuran

DCM

water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGmixture stirred for 10 min
2. 2
   workup.STIRRINGstirred for min
3. 3
   أخرىThe phases were separated
4. 4
   استخلاصthe aqueous layer was extracted with DCM (1000 ml)
5. 5
   تركيزthe organic phases concentrated under reduced pressure
6. 6
   غسيلwashed with DCM in order
7. 7
   استخلاصto extracted impurities
8. 8
   استخلاصextracted with DCM (3×500 ml)
9. 9
   تجفيفthe combined organic phases dried over Na2SO4 before the solvent
10. 10
    أخرىwas removed under reduced pressure

الإجراء التجريبي

(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 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).

المصدر