반응 #46709

반응 방정식

potassium carbonate

4-chlorobutanoyl chloride

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

triethylamine

→

title compound

수율 19.4%

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

수율 19.4%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONthe whole mix
2. 2
   workup.ADDITIONThe reaction mix
3. 3
   기타was evaporated under reduced pressure
4. 4
   기타to 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
   온도was cooled
9. 9
   기타then partitioned between dichloromethane and 0.5M hydrochloric acid
10. 10
    기타the organic layer was evaporated under reduced pressure
11. 11
    기타to give a brown oil which
12. 12
    기타was purified by column chromatography on a 1 g SCX column
13. 13
    세척eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether

실험 절차

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%).

출처