Piperidine → Ethyl 3,4-bis(2-methoxyethoxy)benzoate

HRID 1095003Notes

Reaction equation

HRID 1095003 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1)[CH3:2].[CH2:14]([O:16][C:17](=O)[C:18]1C=C(N2CCCCC2)C=CC=1N)C.[C:32](=[O:35])([O-])[O-].[K+].[K+].N1CCC[CH2:40][CH2:39]1>CC(C)=O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:39][CH2:40][O:35][CH3:32])=[C:7]([O:12][CH2:18][CH2:17][O:16][CH3:14])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8082Piperidine2×HCID 11430Potassium CarbonateHCID 77547Ethyl 3,4-DihydroxybenzoateHCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester

Product 1

HCID 2808992Ethyl 3,4-bis(2-methoxyethoxy)benzoateYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

3,4-Dihydroxy-benzoic acid ethyl ester (compound A′) (2.0 g) was dissolved in acetone (20 ml). Potassium carbonate (4.3 g) and 1-bromo-2-methoxy-ethane (compound D) (5 ml) were added to the solution at room temperature, and the mixture was then stirred at 70° C. for 24 hr. After the completion of the reaction, the reaction solution was allowed to stand for cooling at room temperature, and the reaction system was concentrated under the reduced pressure. Distilled water was added to the residue, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography using a hexane-acetone system to give 3,4-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (3.06 g, yield 93%).

Workup

  1. customAfter the completion of the reaction
  2. temperaturefor cooling at room temperature
  3. concentrationthe reaction system was concentrated under the reduced pressure
  4. additionDistilled water was added to the residue
  5. extractionthe mixture was then subjected to separatory extraction with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialwas dried over sodium sulfate
  8. concentrationwas then concentrated under the reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c7a9a14c1a3f443d9414d55c47afcadd
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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