Triethylamine → (E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenamide

HRID 428139

Reaction equation

HRID 428139 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)[CH:9]=1.C(Cl)(=O)C(C)(C)C.Br.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:37](=[O:41])[CH2:38][NH:39][CH3:40])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]>ClCCl>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:37](=[O:41])[CH2:38][N:39]([CH3:40])[C:16](=[O:18])/[CH:15]=[CH:14]/[C:10]2[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=2)[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 183578301-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanone hydrobromide

Product 1

HCID 20701373(E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenamideYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dichloromethane (50 ml) and triethylamine (2.69 ml, 19.30 mmol) were sequentially added to trans-3-(3-pyridyl)acrylic acid (1.44 g, 9.65 mmol) and stirred for 10 minutes. Then, pivaloyl chloride (1.18 ml, 9.65 mmol) was added and stirred for 13 minutes. 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanone hydrobromide (2.79 g, 9.65 mmol) was dissolved in dichloromethane (4 ml) and triethylamine (1.34 ml, 9.65 mmol), added to the reaction mixture and stirred at room temperature for 30 minutes. After the reaction mixture was washed with water and aqueous saturated sodium bicarbonate solution, the organic phase was dried over magnesium sulfate and the solvent was distilled out under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1) to yield a crude product. The crude product was recrystallized to yield the titled compound (1.84 g, 5.41 mmol, 56%).

Workup

  1. stirringstirred for 13 minutes
  2. stirringstirred at room temperature for 30 minutes
  3. washAfter the reaction mixture was washed with water and aqueous saturated sodium bicarbonate solution
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1)
  7. customto yield a crude product
  8. customThe crude product was recrystallized

Sources & evidence

ORD record
ord-d4cf7afa31954f7aaa77507c51625fd1
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Linked notes

Loading…