Acetic Acid → HCID 19769113, compound

HRID 2081534Notes

Reaction equation

HRID 2081534 reaction equation
C(O)(=[O:3])C.[CH2:5]([O:12][CH2:13][C:14](=O)[CH:15]([CH2:18][CH3:19])[CH:16]=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:21](#[N:25])[CH2:22][C:23]#[N:24].N1CCCCC1>C(O)C>[C:23]([C:22]1[C:21](=[O:3])[NH:25][C:14]([CH2:13][O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:15]([CH2:18][CH3:19])[CH:16]=1)#[N:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 8082PiperidineHCID 19769117HCID 19769117, compound

Product 1

HCID 19769113HCID 19769113, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Acetic acid (2.0 mL, 35 mmol) was added to a solution of crude 4-benzyloxy-3-oxo-2-ethylbutanal (6.4 g, ~24 mmol) and malononitrile (2.22 g, 33 mmol) in ethanol (30 mL) followed by dropwise addition of piperidine (2.37 mL, 24 mmol) to give a dark reddish brown solution. After stirring for 14 hours, a copious precipitate formed. This mixture was warmed at 70° C. for 15 hours and then allowed to cool to room temperature. This blackish mixture was diluted with ethanol and the precipitated product was filtered, rinsed with ethanol and diethyl ether to give off-white product with m.p. of 141°-143° C. Additional material was obtained by evaporation of the filtrate. The residue was extracted into chloroform, and after washing the extract with saturated aqueous NaHCO3, filtered through a pad of charcoal. This amber solution was evaporated and the residue triturated with diethyl ether to give additional product.

Workup

  1. customto give a dark reddish brown solution
  2. customa copious precipitate formed
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered
  5. washrinsed with ethanol and diethyl ether
  6. customto give off-white product with m.p. of 141°-143° C
  7. customAdditional material was obtained by evaporation of the filtrate
  8. extractionThe residue was extracted into chloroform
  9. washafter washing the
  10. extractionextract with saturated aqueous NaHCO3
  11. filtrationfiltered through a pad of charcoal
  12. customThis amber solution was evaporated
  13. customthe residue triturated with diethyl ether
  14. customto give additional product

Sources & evidence

ORD record
ord-c73971bc64b149278771792863b78884
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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