1-Methylpiperazine → 5-Fluoro-6-(4-methylpiperazinyl)isatin

HRID 1756558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756558
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1F)[NH:7][C:6](=[O:12])[C:5]2=[O:13].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[NH:7][C:6](=[O:12])[C:5]2=[O:13]

Komponenten

5

Edukt 2

HCID 531671-MethylpiperazineHCID 19263085,6-difluoro-2,3-dihydro-1H-indole-2,3-dione

Produkt 1

HCID 193907095-Fluoro-6-(4-methylpiperazinyl)isatinAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5,6-difluoroisatin (1.0 g, 5 mmol) in 50 mL of dimethyl sulfoxide was added N-methylpiperazine (5.47 g, 50 mmol). The mixture was stirred for 4 h at room temperature and the crude reaction mixture was diluted with ethyl acetate. The organic solution was washed with saturated sodium bicarbonate. The organic layers were separated and concentrated to give the title compound in 72% yield: mp 150° C. (dec); 1H NMR (300 MHz, DMSO-d6)δ 10.8 (br s, 1H), 7.3 (d, 1H), 6.4 (d, 1H), 2.25 (s, 3H), 2.2 (m, 4H), 2.1 (m, 4H).

Aufarbeitung

  1. customthe crude reaction mixture
  2. washThe organic solution was washed with saturated sodium bicarbonate
  3. customThe organic layers were separated
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fe055647377f40788f46b7a0bc724a93
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05441955

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