Morpholine → 4-{[5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]methyl}morpholine

HRID 6938

Reaktionsgleichung

Reaktionsgleichung von HRID 6938
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[C:9]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:18]([CH2:27]Cl)=[N:17][N:16]=2)=[CH:11][CH:10]=1>CN(C)C=O>[C:9]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:18]([CH2:27][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:17][N:16]=2)=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 24758Sodium hydrideHCID 220192313-Biphenyl-4-yl-5-chloromethyl-4-(2-fluorophenyl)-4H-1,2,4-triazole

Produkt 1

HCID 220192434-{[5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]methyl}morpholineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Morpholine (0.599 ml) was dissolved in N,N-dimethylformamide (6 ml), followed by addition of sodium hydride (60%, 275 mg) under ice cooling, and stirred at the same temperature for 30 minutes. Under ice cooling, 3-biphenyl-4-yl-5-chloromethyl-4-(2-fluorophenyl)-4H-1,2,4-triazole (599 mg) was added to the reaction solution, and stirred at ambient temperature for 17 hours. After the reaction solution was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent: toluene/acetone=3/2 to 1/1), and recrystallized from a mixture solution of n-hexane and ethyl acetate, to afford the entitled compound as white crystal (211 mg, 74%). The physico-chemical values are as follows.

Aufarbeitung

  1. stirringstirred at ambient temperature for 17 hours
  2. concentrationAfter the reaction solution was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  3. additionwas added to the resulting residue
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel chromatography (eluent: toluene/acetone=3/2 to 1/1)
  8. customrecrystallized from a mixture solution of n-hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7794f3c01c4a42198c2584e503f849f8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084164B2

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