Diglyme → TJN-331

HRID 428133Notes

Reaction equation

HRID 428133 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([O:11]C)=O)[CH:2]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:18][CH2:19][NH:20][CH3:21].[H-].[Na+].COCCOCCOC>O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:18][CH2:19][N:20]([CH3:21])[C:9](=[O:11])/[CH:8]=[CH:7]/[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8150DiglymeHCID 24758Sodium hydrideHCID 77039N-MethylhomoveratrylamineHCID 53576873-Pyridineacrylic acid, methyl ester

Product 1

HCID 9818748TJN-331Yield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl trans-3-(3-pyridyl)acrylate (326 mg), 3,4-dimethoxy-N-methylphenethylamine (390 mg), 60% sodium hydride (80 mg) and diethylene glycol dimethyl ether (2 ml) was stirred at room temperature for 24 hours. Water was added to the reaction mixture, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. After the solvent was distilled out under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=50:1) and recrystallized to yield the titled compound (278 mg, 43%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationAfter the solvent was distilled out under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)
  6. customrecrystallized

Sources & evidence

ORD record
ord-e294c8625fed4dccadecbf005de2f81d
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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