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

HRID 1819348Notes

Reaction equation

HRID 1819348 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

HCID 688298583-[4-(3-Benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrileYield 55.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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%.

Workup

  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)

Sources & evidence

ORD record
ord-65d19433d32e41f382eda52b3079dbb2
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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