Piperidine → 2-Propenoic acid,2-cyano-3-(3-pyridinyl)-

HRID 868359Notes

Reaction equation

HRID 868359 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]([CH2:11][C:12]([OH:14])=[O:13])#[N:10].N1CCCCC1>C(O)C>[C:9]([C:11](=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:12]([OH:14])=[O:13])#[N:10]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 9740Cyanoacetic acidHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 27637192-Propenoic acid,2-cyano-3-(3-pyridinyl)-Yield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3.8 g of 3-pyridinecarbaldehyde, 3.0 g of cyanoacetic acid, 3.0 g of piperidine, and 30 ml of ethanol is stirred at 100° C. for 4 hours. The reaction mixture is concentrated, and 20 ml of water is added. The mixture is adjusted to pH 4.5 with 10% hydrochloric acid. The resulting precipitate is collected and recrystallized from ethanol to give 3.8 g of the title compound, m.p. 223°-227° C.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition20 ml of water is added
  3. customThe resulting precipitate is collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5f6dddd4f7944301b9d4a14d11d22f24
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

Loading…