Reaction #46709

Reaction equation

potassium carbonate

4-chlorobutanoyl chloride

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

triethylamine

→

title compound

Yield 19.4%

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

Yield 19.4%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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%).

Source