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

HRID 1178524Notes

Reaction equation

HRID 1178524 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][CH2:24][CH3:25])=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)[CH3:14].[C:26](=[O:29])([O-:28])[O-].[Cs+].[Cs+].[OH-:32].[Na+]>CN(C=O)C>[C:18]([OH:22])(=[O:32])/[CH:19]=[CH:20]/[C:26]([OH:28])=[O:29].[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][CH2:24][CH3:25])[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 936554-Chloro-2-fluorobenzonitrileHCID 137809963-Dimethylaminomethyl-2-propylphenol hydrobromide

Product 1

HCID 219304244-Chloro-2-(3-dimethylaminomethyl-2-propylphenoxy)-benzonitrile fumarate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.90 g, 5.8 mmol), 3-dimethylaminomethyl-2-propylphenol hydrobromide (1.58 g, 5.8 mmol) and cesium carbonate (3.94 g, 12.1 mmol) were heated with stirring in dry DMF (6 mL) at 50° C. for 18 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 (1×), water (2×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to give a yellow oil (1.77 g), which was purified by chromatography to yield 4-chloro-2-(3-dimethylaminomethyl-2-propylphenoxy)-benzonitrile (1.53 g, 81%) as a pale yellow oil. A small portion (100 mg) was converted into the fumarate salt (63 mg, 47%).

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 (1×), water (2×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-310668989f064fc3a268c7c7b4dc788f
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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