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

HRID 215789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 215789
[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-1c40c7e578ec4c259002f0939875545d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193185B2

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