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

HRID 489921

Reaktionsgleichung

Reaktionsgleichung von HRID 489921
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 693731484-(3-Fluoro-4-methoxylphenyl)-3-pyridyl-3-butene-2-oneAusbeute 393,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f9ced75ef53c4362afa8e12efbbe0011
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06979686B1

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