Sodium Carbonate → 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

HRID 1773858

Reaktionsgleichung

Reaktionsgleichung von HRID 1773858
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[CH2:9]([N:17]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=[C:18]1[CH:28]=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CS(O)(=O)=O.C(Cl)(Cl)Cl>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([O:1][CH:28]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][CH2:9][N:17]3[C:18]2=[N:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:21]3)[CH2:3][CH2:4]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 660484-Piperidinol, 1-methyl-HCID 867039471-Phenethyl-4-phenyl-imidazole-2-carbaldehyde

Produkt 1

HCID 726957794-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6395Methanesulfonic AcidLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-N-methylpiperidine (275 mg, 2.39 mmoles) in methanesulfonic acid (2 mL) at 0° C. is added a solution of 1-phenethyl-4-phenyl-imidazole-2-carbaldehyde (example 4B) (250 mg, 0.904 mmoles) in chloroform (2 mL). The reaction mixture is stirred at room temperature overnight, then heated to reflux for 6 h. A saturated solution of Na2CO3 is added to reach pH 10. The aqueous phase is extracted three times with CH2Cl2. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH) (90:10) to give 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene melting at 113° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. extractionThe aqueous phase is extracted three times with CH2Cl2
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a98f6ab652fb447c90e4a58ed8cc0356
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255101B2

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