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

HRID 4001

Reaktionsgleichung

Reaktionsgleichung von HRID 4001
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.C(N(CC)CC)C.Cl.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32](Cl)=[O:33])[CH2:28][CH2:27]1.[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39]>C(Cl)(Cl)Cl.C(O)C.O>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39].[N:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:32]([N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)=[O:33])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Komponenten

8

Edukt 4

HCID 8471Triethylamine2×HCID 444266Maleic AcidHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochloride2×HCID 125191182-(2,3-Dihydro-1H-indol-1-YL)phenylamine

Produkt 1

HCID 70406277N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide MaleateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwere added
  2. temperatureAfter refluxing overnight (total of 25 hrs)
  3. temperaturethe reaction was cooled
  4. customThe layers were separated
  5. washthe organic phase was washed twice with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in 100 ml of absolute ethanol
  9. waitAfter several hours
  10. customthe crystals were collected
  11. washwashed with ethanol
  12. customdried
  13. customto afford 19.2 g (43%)

Quellen und Nachweise

ORD-Eintrag
ord-1d2813a33d28473591d96037dace2e49
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723007

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