Cesium carbonate → 4-Chloro-2-(3-dimethylaminomethyl-2-ethylphenoxy)benzonitrile fumarate

HRID 1243738Notes

Reaction equation

HRID 1243738 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.Br.[CH3:12][N:13]([CH2:15][C:16]1[C:17]([CH2:23][CH3:24])=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)[CH3:14].[C:25](=[O:28])([O-:27])[O-].[Cs+].[Cs+].[OH-:31].[Na+]>CN(C=O)C>[C:18]([OH:22])(=[O:31])/[CH:19]=[CH:20]/[C:25]([OH:27])=[O:28].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][N:13]([CH3:14])[CH3:12])[C:17]=2[CH2:23][CH3:24])[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 936554-Chloro-2-fluorobenzonitrileHCID 137809943-Dimethylaminomethyl-2-ethylphenol hydrobromide

Product 1

HCID 219303484-Chloro-2-(3-dimethylaminomethyl-2-ethylphenoxy)benzonitrile fumarate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.82 g, 5.27 mmol), 3-dimethylaminomethyl-2-ethylphenol hydrobromide (1.37 g, 5.27 mmol) and cesium carbonate (3.43 g, 10.5 mmol) were heated with stirring in dry DMF (8 mL) at 50° C. for 4 h. The reaction mixture was cooled, poured into 0.1N sodium hydroxide solution and extracted with diethyl ether. The ether layer was separated, washed with 1N sodium hydroxide solution (2×), water (3×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to give a yellow oil (1.86 g), which was purified by chromatography to yield 4-chloro-2-(3-dimethylaminomethyl-2-ethylphenoxy)benzonitrile (1.29 g, 78%) as a pale yellow oil. A small portion (98 mg) was converted into the fumarate salt (80 mg, 60%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with diethyl ether
  3. customThe ether layer was separated
  4. washwashed with 1N sodium hydroxide solution (2×), water (3×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c9f397cee59b4bca91e2767aa7bf3a2e
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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