Cesium carbonate → HCID 68525258, Verbindung

HRID 1932427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1932427
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][O:14][CH3:15])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([C:2]2[CH:3]=[CH:4][C:5]([O:12][CH2:13][O:14][CH3:15])=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 759941-BenzylpiperazineHCID 634876Binap, (A+-)-HCID 20827868HCID 20827868, Verbindung

Produkt 1

HCID 68525258HCID 68525258, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of methyl 5-chloro-2-methoxymethoxybenzoate (1.45 g, 6.29 mmol) and 1-benzylpiperazine (1.66 g, 9.43 mmol) in toluene (50 mL) were added palladium acetate (28 mg, 0.126 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (157 mg, 0.252 mmol) and cesium carbonate (3.07 g, 9.43 mmol), and the resulting solution was refluxed for 3 hours. Water was added to the resulting solution, and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2), to thereby yield 400 mg of the title compound.

Aufarbeitung

  1. temperaturethe resulting solution was refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-f41ef6500ace4e438c81c76975516bea
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188277B2

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