Piperidine → (E)-5-((2,6-Dimethoxystyrylsulfonyl)methyl)-2-methoxy-3-nitropyridine

HRID 72657

Reaktionsgleichung

Reaktionsgleichung von HRID 72657
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][S:10]([CH2:13][C:14](O)=O)(=[O:12])=[O:11])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18].N1CCCCC1.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[C:29]=1C=O>N1C=CC=CC=1>[CH3:26][O:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[C:29]=1/[CH:14]=[CH:13]/[S:10]([CH2:9][C:6]1[CH:5]=[C:4]([N+:17]([O-:19])=[O:18])[C:3]([O:2][CH3:1])=[N:8][CH:7]=1)(=[O:12])=[O:11]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 964042,6-DimethoxybenzaldehydeHCID 679948792-((6-Methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetic acid

Produkt 1

HCID 86690905(E)-5-((2,6-Dimethoxystyrylsulfonyl)methyl)-2-methoxy-3-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 2-((6-methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetic acid (0.29 g, 1 mmol) in dry pyridine (20 mL) was treated with piperidine (2 mL), followed by 2,6-dimethoxybenzaldehyde (0.17 g, 1 mmol). The mixture was refluxed for 6 h, and evaporated to dryness. The residue was purified by column chromatography using a mixture of EtOAc/PE (1:2, v/v) to yield the titled compound. HR-MS (ESI+) m/z 394.8362; C17H18N2O7S requires 394.0835.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 6 h
  2. customevaporated to dryness
  3. customThe residue was purified by column chromatography
  4. additiona mixture of EtOAc/PE (1:2

Quellen und Nachweise

ORD-Eintrag
ord-2a9ca364a46c485f84a000b022bec748
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829003B2

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