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

HRID 1243742노트

반응식

HRID 1243742 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c0102f27e81947789f2224ba25d61916
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119122B2

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