Pipecolic Acid → HCID 15045341, compound

HRID 1769668Notes

Reaction equation

HRID 1769668 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].[C:10](=O)([O-])O.[Na+].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26](Cl)=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>C(#N)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[C:7]([O:9][CH3:10])=[O:8])=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 849Pipecolic AcidHCID 516892Sodium BicarbonateHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 15045341HCID 15045341, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.00 g of piperidine-2-carboxylic acid was dissolved into an aqueous 80 ml solution of saturated sodium hydrogen carbonate and stirred at a room temperature. 20 ml of an acetonitrile solution of 9.2 g of 3,4-dimethoxyphenyl acetyl chloride was dropped and stirred for 30 min. After washing the aqueous layer with ethyl acetate, the aqueous layer was adjusted to about pH 2 with concentrated hydrochloric acid and extracted with chloroform. Chloroform was distilled off and the resultant residue was refluxed for 6 hours with addition of 150 ml of methanol and 0.5 ml of concentrated sulfuric acid. After distilling off methanol, an aqueous diluted solution of sodium hydrogen carbonate was added and extracted with ethyl acetate. After drying with anhydrous magnesium sulfate, the solvent was distilled off and the residue was purified on silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) to obtain 3.94 g of the above-captioned compound as yellow oil (yield: 32%).

Workup

  1. stirringstirred for 30 min
  2. washAfter washing the aqueous layer with ethyl acetate
  3. extractionextracted with chloroform
  4. distillationChloroform was distilled off
  5. temperaturethe resultant residue was refluxed for 6 hours with addition of 150 ml of methanol and 0.5 ml of concentrated sulfuric acid
  6. distillationAfter distilling off methanol
  7. additionan aqueous diluted solution of sodium hydrogen carbonate was added
  8. extractionextracted with ethyl acetate
  9. dry with materialAfter drying with anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off
  11. customthe residue was purified on silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0f95cf2eff8847149136c97dd44b6d3a
Source dataset
uspto-grants-1995_01
Patent number
US05382595

Reaction notes

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