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

HRID 1243742
Notes
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Reaction equation

HRID 1243742 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-c0102f27e81947789f2224ba25d61916
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07119122B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes