Hydrochloric Acid → HCID 86590729, compound

HRID 353676

Reaction equation

HRID 353676 reaction equation
[C:1]([CH2:3][C:4]([O:6]C)=O)#N.[CH2:8]([CH:10]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11]N)[CH3:9].C(OCC)(=O)CC(C)=O.[NH:26]1CCC[CH2:28][CH2:27]1.Cl>CO>[CH2:8]([CH:10]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][C:3]1[C:4](=[O:6])[NH:26][CH:27]=[CH:28][CH:1]=1)[CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 77192-EthylhexylamineHCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 8868Ethyl Acetoacetate

Product 1

HCID 86590729HCID 86590729, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

Into a 1 liter round-bottom flask equipped with stirrer and Dean Stark trap was charged methyl cyanoacetate (99 grams, 1 mol; obtained from Sigma-Aldrich Co., Milwaukee, Wis.), followed with methanol solvent (150 milliliters), and the mixture was stirred briefly. 2-Ethylhexylamine (130 grams, 1 mol) was slowly added into this mixture, followed with the sequential addition of ethyl acetoacetate (130 grams, 1 mol; obtained from Sigma-Aldrich Co.), and then piperidine (85 grams, 1 mol; obtained from Sigma-Aldrich Co.). The solution was stirred and heated at 100° C. for 12 hours, and then was cooled to room temperature. The mixture was diluted with 2,500 milliliters of methanol and acidified carefully with concentrated hydrochloric acid until a large amount of precipitate had formed. The precipitate was filtered by vacuum and repeatedly washed with deionized water and filtered until the filtrate was of neutral pH. The crude material was recrystallized in warm methanol to afford 170 grams (65 percent yield) of 2-ethylhexyl pyridone as a white solid.

Workup

  1. customInto a 1 liter round-bottom flask equipped with stirrer
  2. stirringThe solution was stirred
  3. temperaturewas cooled to room temperature
  4. customhad formed
  5. filtrationThe precipitate was filtered by vacuum
  6. washrepeatedly washed with deionized water
  7. filtrationfiltered until the filtrate
  8. customThe crude material was recrystallized in warm methanol

Sources & evidence

ORD record
ord-364aed43fef1480284ccd1eda5d3c21e
Source dataset
uspto-grants-2004_06
Patent number
US06755902B2

Linked notes

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