Ethanol → HCID 67327913, Verbindung

HRID 1853950

Reaktionsgleichung

Reaktionsgleichung von HRID 1853950
CN([CH:4]=[C:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[CH3:21])[CH2:6]1)C.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=1.[C:33]([O-:36])(=[O:35])C.[Na+].[CH2:38]([OH:40])[CH3:39]>O>[CH3:23][O:36][C:33](=[O:35])[C:16]1[CH:15]=[CH:14][C:13]([CH3:21])=[C:12]([N:7]2[CH2:6][CH2:5][C:10]3([O:11][CH2:39][CH2:38][O:40]3)[CH2:9][CH2:8]2)[CH:17]=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]2[N:32]=[CH:4][C:5]3[CH2:6][N:7]([C:12]4[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=4[CH3:21])[CH2:8][CH2:9][C:10]=3[N:31]=2)=[CH:27][CH:28]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 673288983-Dimethylaminomethylene-1-(2-methyl-5-nitrophenyl)piperidin-4-oneHCID 178512500HCID 178512500, Verbindung

Produkt 2

HCID 67327913HCID 67327913, VerbindungHCID 673546753-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-4-methyl-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 3-Dimethylaminomethylene-1-(2-methyl-5-nitro-phenyl)-piperidin-4-one (12.06 gm, 41.7 mmol)[as prepared in reference 1] in Ethanol (250 ml) were added N-(4-Chloro-phenyl)-guanidine (28.32 gm, 167 mmol) and sodium acetate (27.32 gm, 334 mmol) and solution was heated under reflux for 12 hours. After cooling to room temperature, the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was washed with brine, dried [sodium sulfate] and concentrated under vacuum. The crude product obtained was further purified by silica gel chromatography using 5-10% Methanol/Chloroform as eluent to give pure desired product [11] i.e., (4-Chloro-phenyl)-[6-(2-methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-amine as yellow solid. (Yield: 2.50 gm, 15.2%)

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried [sodium sulfate]
  6. concentrationconcentrated under vacuum
  7. customThe crude product obtained
  8. customwas further purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-47ade73e82444c86a09c1581f508b7cf
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962637B2

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