Ethyl cyanoacetate → HCID 408695, compound

HRID 1285514Notes

Reaction equation

HRID 1285514 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].C([O-])(=O)C.[NH4+].[OH-].[Na+]>C1C=CC=CC=1.O>[CH2:15]([O:14][C:12](=[O:13])[C:11](=[C:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[C:9]#[N:10])[CH3:16]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 517165Ammonium Acetate

Product 1

HCID 408695HCID 408695, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture containing 1.05 g (9.27 mmoles) of 1-methyl-4-piperidone (commercially available: Aldrich Chemical Co., 1.00 mL (9.4 mmoles) of ethyl cyanoacetate, and 148 mg of ammonium acetate in 35 mL of benzene was heated at reflux for 3 hours with continuous azeotropic removal of water by means of a Dean-Stark trap. The product was isolated by cooling the mixture to room temperature, pouring it into 30 mL of 2:1 (v/v) 1M aqueous NaOH:saturated brine, and extraction with ether. The organic extracts were washed with 10% aqueous sodium chloride solution, then were dried over anhydrous sodium sulfate and subsequently filtered. Removal of the ether and benzene by evaporation at reduced pressure afforded 1.46 g (76% yield) of cyanoester 9.

Workup

  1. customThe product was isolated
  2. extractionsaturated brine, and extraction with ether
  3. washThe organic extracts were washed with 10% aqueous sodium chloride solution
  4. dry with materialwere dried over anhydrous sodium sulfate
  5. filtrationsubsequently filtered
  6. customRemoval of the ether and benzene
  7. customby evaporation at reduced pressure

Sources & evidence

ORD record
ord-4e336ebded9e41cfa0963fd19192c2fe
Source dataset
uspto-grants-1986_01
Patent number
US04567265

Reaction notes

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