3-Bromobenzonitrile → HCID 68831348, compound

HRID 1727153Notes

Reaction equation

HRID 1727153 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH:17]1[CH2:21][NH:20][C:19](=[O:22])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[C:35]#[N:36].[C@@H]1(N)CCCC[C@H]1N>CCOC(C)=O.[Cu]I.O1CCOCC1.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH:17]1[CH2:21][N:20]([C:32]2[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=2)[C:35]#[N:36])[C:19](=[O:22])[CH2:18]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 68829062HCID 68829062, compound

Product 1

HCID 68831348HCID 68831348, compoundYield 81.2%

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
110 °C

Procedure

4-(2-Benzyloxy-4-methoxyphenyl)-pyrrolidin-2-one (2.0 g. 6.8 mmol), potassium phosphate (2.56 g, 1.8 eq), and 3-bromobenzonitrile (1.82 g, 1.5 eq) was added to a flask under N2. The mixture was charged with 10 mL DMF and 10 mL dioxane followed by the addition of 1,2-trans-cyclohexanediamine (100 μL) and CuI (180 mg). The mixture was heated at 110° C. for 20 h and cooled down to r.t. Next the mixture was diluted with 150 mL EtOAc, washed with sat. NH4Cl, water, and brine, and then dried. After concentration, the residue was purified on silica gel (EtOAc: Hexane=3:1) to give 2.2 g of the desired product. Yield: 81%.

Workup

  1. temperaturecooled down to r.t
  2. washwashed with sat. NH4Cl, water, and brine
  3. customdried
  4. concentrationAfter concentration
  5. customthe residue was purified on silica gel (EtOAc: Hexane=3:1)

Sources & evidence

ORD record
ord-6c108a28afed48d6891793f7e21ff866
Source dataset
uspto-grants-2009_02
Patent number
US07495016B2

Reaction notes

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