3-Bromobenzonitrile → 3-[4-(3-Benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

HRID 1727148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727148
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>CN(C=O)C.O1CCOCC1.[Cu]I.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][N:18]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])[C:17](=[O:20])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

9

Edukt 4

HCID 233813-BromobenzonitrileHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 688307524-[3-(Benzyloxy)phenyl]pyrrolidin-2-one

Produkt 1

HCID 688298583-[4-(3-Benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrileAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-(3-benzyloxyphenyl)-pyrrolidin-2-one (1.8 g, 6.7 mmol), 3-bromobenzonitrile (1.83 g, 1.5 eq) and potassium phosphate (2.6 g, 1.8 eq) was created in a dry flask with a stir bar under N2. This mixture was dissolved in 10 mL DMF and 10 mL dioxane. To this solution was added 60 μL of 1,2-trans-cyclohexanediamine and CuI (100 mg). The solution was stirred and heated at 100° C. under N2 for 20 h, and then cooled down to r.t. EtOAc (100 mL) was added and the mixture was filtered, washed with NH4Cl solution, water and brine. The solution was also dried over MgSO4 and concentrated under a reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3) to give 1.36 g of the desired product. Yield: 55%.

Aufarbeitung

  1. customwas created in a dry flask with a stir bar under N2
  2. temperaturecooled down to r.t
  3. filtrationthe mixture was filtered
  4. washwashed with NH4Cl solution, water and brine
  5. dry with materialThe solution was also dried over MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-be3ae6e1ba01499bb62f8b527af4de23
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495016B2

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