Piperidine → 4-(3-Fluoro-4-methoxylphenyl)-3-pyridyl-3-butene-2-one

HRID 861029Notes

Reaction equation

HRID 861029 reaction equation
N1C=C[C:4]([CH2:7][C:8](=[O:10])[CH3:9])=CC=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])C=O.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:13]=[C:14]([C:25]2[CH:26]=[CH:27][N:22]=[CH:23][C:24]=2[CH2:9][C:8](=[O:10])[CH:7]=[CH2:4])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

5

Reactant 3

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

Product 1

HCID 693731484-(3-Fluoro-4-methoxylphenyl)-3-pyridyl-3-butene-2-oneYield 393.2%

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-methoxylphenyl)-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-6ca84ced18b7445aaddd78c9deaecef5
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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