反应 #46709

反应方程式

potassium carbonate

4-chlorobutanoyl chloride

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

triethylamine

→

title compound

收率 19.4%

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

收率 19.4%

溶剂

dichloromethane

反应条件

后处理

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

实验过程

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%).

来源