반응 #4097

반응 방정식

1-(2-aminophenyl)indoline

triethylamine

4-methyl-1-piperazinecarbonyl chloride hydrochloride

maleic acid

triethylamine

4-methyl-1-piperazinecarbonyl chloride hydrochloride

→

pure salt

수율 53.0%

N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide Maleate

수율 53.0%

용매

chloroform

ethanol

water

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   온도After refluxing overnight (total of 25 hrs)
3. 3
   온도the reaction was cooled
4. 4
   기타The layers were separated
5. 5
   세척the organic phase was washed twice with water
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   workup.DISSOLUTIONThe residue was dissolved in 100 ml of absolute ethanol
9. 9
   workup.WAITAfter several hours
10. 10
    기타the crystals were collected
11. 11
    세척washed with ethanol
12. 12
    기타dried
13. 13
    기타to afford 19.2 g (43%)

실험 절차

To a stirred solution, under nitrogen, of 21.0 g (0.10 mole) of 1-(2-aminophenyl)indoline and 30.4 g (0.30 mole) of triethylamine in 400 ml of chloroform was added 29.9 g (0.15 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over about 5 minutes. The reaction was refluxed for 6 hours when an additional 10.1 g (0.10 mole) of triethylamine and 19.9 g (0.10 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride were added. After refluxing overnight (total of 25 hrs), the reaction was cooled, treated with 400 ml water, and stirred vigorously for 15 minutes. The layers were separated and the organic phase was washed twice with water, dried over Na2SO4, and concentrated in vacuo. The residue was dissolved in 100 ml of absolute ethanol and treated in one portion with a warm solution of 13.2 g (0.11 mole) of maleic acid in 50 ml of ethanol. After several hours, the crystals were collected, washed with ethanol, and dried to afford 19.2 g (43%), of product, m.p. 158° dec. An additional 4.5 g of pure salt was obtained from the mother liquor making the total amount of product 23.7 g and the yield 53%. 3.0 g of product were recrystallized from ethanol to provide 2.80 g of N-[2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboximide maleate.

출처