Piperidine → HCID 65574170, compound

HRID 1790307Notes

Reaction equation

HRID 1790307 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](CC(=O)C)=[CH:3][CH:2]=1.F[C:12]1[CH:13]=C(C=[CH:18][C:19]=1[O:20]C)C=O.N1CCCCC1>C1(C)C=CC=CC=1>[N:1]1[CH:2]=[CH:3][CH:4]=[C:5]([CH2:18][C:19](=[O:20])[CH:12]=[CH2:13])[CH:6]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 676963-Fluoro-p-anisaldehydeHCID 805524-Pyridinylacetone

Product 1

HCID 65574170HCID 65574170, compoundYield 146.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-pyridylacetone (1.0 g, 7.4 mmol), 3-fluoro-p-anisaldehyde (1.25 g, 8.1 mmol), and piperidine (0.13 g, 1.5 mmol) in toluene (50 ml) was heated to reflux. After 18 hours, the reaction was cooled to room temperature and the solvent was removed under reduced pressure. The crude product (3.0 g) was purified by column chromatography (silica gel, 65:35 ethyl acetate/hexane) to give 4-(3-fluoro-4-methoxy]phenyl)-3-pyridyl-3-butene-2-one as a pale yellow solid (1.60 g, 80%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe crude product (3.0 g) was purified by column chromatography (silica gel, 65:35 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4ba49e669c8944568145ff09ba5e9264
Source dataset
uspto-grants-2006_07
Patent number
US07071198B1

Reaction notes

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