تفاعل #2569

معادلة التفاعل

N-methylmorpholine

isobutyl chloroformate

4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid

ammonia

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title compound

المردود 50.9%

4-Carbamoyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

المردود 50.9%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةIn an atmosphere of argon and with cooling in an ice bath
2. 2
   درجة الحرارةwas cooled in an ice bath
3. 3
   workup.WAITfollowed by additional 10 minutes
4. 4
   workup.STIRRINGof stirring at room temperature
5. 5
   استخلاصThe reaction mixture was extracted with methylene chloride
6. 6
   تجفيفthe resulting organic layer was dried on anhydrous sodium carbonate
7. 7
   أخرىThereafter, the solvent was removed by evaporation
8. 8
   أخرىthe resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1)

الإجراء التجريبي

In an atmosphere of argon and with cooling in an ice bath, 4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid (63 mg, 0.117 mmol) was dissolved in THF (1 ml) to which were subsequently added dropwise N-methylmorpholine (14 μl, 0.13 mmol) and isobutyl chloroformate (16.8 μl, 0.13 mmol). After 15 minutes of stirring at room temperature, 28% liquid ammonia (0.5 ml) was added to the reaction solution which was cooled in an ice bath, followed by additional 10 minutes of stirring at room temperature. The reaction mixture was extracted with methylene chloride, and the resulting organic layer was dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1) to obtain 32 mg (50.9%) of the title compound in the form of light yellow oil.

المصدر