Piperidine → beta-(2,5-Dimethoxyphenyl)acrylonitrile

HRID 1730435Notes

Reaction equation

HRID 1730435 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=O.[C:13]([CH2:15]C(O)=O)#[N:14].N1CCCCC1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=[CH:15][C:13]#[N:14]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 9740Cyanoacetic acidHCID 667262,5-Dimethoxybenzaldehyde

Product 1

HCID 3420939beta-(2,5-Dimethoxyphenyl)acrylonitrileYield 69.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 166 g of 2,5-dimethoxybenzaldehyde, 76 g of cyanoacetic acid, 5 ml of piperidine and 400 ml of pyridine was heated at 80° C understirring for 2 hours and then refluxed with heating at 140° C for 5 hours. After the reaction, the mixture was cooled to room temperature and poured into 2 liters of ice water. The precipitated crystals were filteredout and recrystallized from ethanol to give 117 g of the end product havinga melting point of 70 ~ 71° C (yield 62%).

Workup

  1. temperaturerefluxed
  2. temperaturewith heating at 140° C for 5 hours
  3. customAfter the reaction
  4. temperaturethe mixture was cooled to room temperature
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-724012c9a06c452e95f24d21c818d57d
Source dataset
uspto-grants-1976_11
Patent number
US03992449

Reaction notes

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