Triethylamine → HCID 18473809, compound

HRID 2227489Notes

Reaction equation

HRID 2227489 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:16][NH:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(P(C#N)(CC)=O)C.C(N(CC)CC)C>CN(C)C=O.O>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11](=[O:13])[N:17]([CH3:16])[CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:14][CH:15]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 883933-(Methylaminomethyl)pyridineHCID 13586794Diethylphosphorylcyanide

Product 1

HCID 18473809HCID 18473809, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.03 g of 4-acetoxycinnamic acid and 0.61 g of 3-(methylaminomethyl)pyridine were dissolved in 5 ml dimethylformamide, and then stirred with 0.90 ml diethylphosphoryl cyanide and subsequently with 0.75 ml triethylamine on ice for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, washed with brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a residue, which was then purified via column chromatography on silica gel (dichloromethane:methanol=30:1) to provide 4[(E)-2-[N-methyl-N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl acetate (1.50 g).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give a residue, which
  6. customwas then purified via column chromatography on silica gel (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-dda720d508b34536be96da91d938d03c
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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