反応 #46709

反応方程式

potassium carbonate

4-chlorobutanoyl chloride

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

triethylamine

→

title compound

収率 19.4%

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

収率 19.4%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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%).

出典