تفاعل #46709

معادلة التفاعل

potassium carbonate

4-chlorobutanoyl chloride

N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

triethylamine

→

title compound

المردود 19.4%

N-(5-{3-[(2-oxo-1-pyrrolidinyl)methyl]phenyl}-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

المردود 19.4%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONthe whole mix
2. 2
   workup.ADDITIONThe reaction mix
3. 3
   أخرىwas evaporated under reduced pressure
4. 4
   أخرىto remove the dichloromethane
5. 5
   workup.ADDITIONdimethylformamide was added (5 ml)
6. 6
   workup.STIRRINGthe mix stirred at 100° C. for 2 h
7. 7
   workup.ADDITIONThe reaction mix
8. 8
   درجة الحرارةwas cooled
9. 9
   أخرىthen partitioned between dichloromethane and 0.5M hydrochloric acid
10. 10
    أخرىthe organic layer was evaporated under reduced pressure
11. 11
    أخرىto give a brown oil which
12. 12
    أخرىwas purified by column chromatography on a 1 g SCX column
13. 13
    غسيلeluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

الإجراء التجريبي

A solution of N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide (69 mg, 0.2 mmol) in dichloromethane (5 ml) was treated with triethylamine (40 mg, 0.4 mmol), followed by 4-chlorobutanoyl chloride (32 mg, 0.22 mmol) and the whole mix stirred at room temperature under argon for 1 h. The reaction mix was evaporated under reduced pressure to remove the dichloromethane and then dimethylformamide was added (5 ml) followed by potassium carbonate (60 mg, 0.43 mmol) and the mix stirred at 100° C. for 2 h. The reaction mix was cooled then partitioned between dichloromethane and 0.5M hydrochloric acid, and the organic layer was evaporated under reduced pressure to give a brown oil which was purified by column chromatography on a 1 g SCX column eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether to give the title compound as a beige solid (16 mg, 19%).

المصدر