1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 18675007, compound

HRID 1634888Notes

Reaction equation

HRID 1634888 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl.[CH2:23](N=C=NCCCN(C)C)C>CO.ClCCl>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21][CH3:23])=[O:20])[CH:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18674969HCID 18674969, compound

Product 1

HCID 18675007HCID 18675007, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-(3,4,5-Trimethoxyphenyl)pyridine-2-carboxylic acid (587 mg) was dissolved in methanol (2 mL) and dichloromethane (8 mL), and to the solution 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (583 mg) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. After the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure, the residue was purified by column chromatography on silica gel (chloroform:methanol=40:1) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washAfter the organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-cac010a65fe244bfb1a2d03046bdf147
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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