Reaktion #4097

Reaktionsgleichung

1-(2-aminophenyl)indoline

triethylamine

4-methyl-1-piperazinecarbonyl chloride hydrochloride

maleic acid

triethylamine

4-methyl-1-piperazinecarbonyl chloride hydrochloride

→

pure salt

Ausbeute 53.0%

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

Ausbeute 53.0%

Lösungsmittel

chloroform

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   TemperaturAfter refluxing overnight (total of 25 hrs)
3. 3
   Temperaturthe reaction was cooled
4. 4
   SonstigeThe layers were separated
5. 5
   Waschenthe organic phase was washed twice with water
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   workup.DISSOLUTIONThe residue was dissolved in 100 ml of absolute ethanol
9. 9
   workup.WAITAfter several hours
10. 10
    Sonstigethe crystals were collected
11. 11
    Waschenwashed with ethanol
12. 12
    Sonstigedried
13. 13
    Sonstigeto afford 19.2 g (43%)

Vorschrift

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.

Quelle