Piperidine → Pyrido[2,3-b]pyrazine-6,7-dicarboxylic acid, diethyl ester

HRID 54190

Reaktionsgleichung

Reaktionsgleichung von HRID 54190
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:2][C:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=O.N1CCCCC1.[NH2:20][C:21]1[C:22]([CH:27]=O)=[N:23][CH:24]=[CH:25][N:26]=1>C1(C)C=CC=CC=1>[N:23]1[CH:24]=[CH:25][N:26]=[C:21]2[N:20]=[C:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:2]([C:1]([O:11][CH2:12][CH3:13])=[O:10])=[CH:27][C:22]=12

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 66951Diethyl oxalacetateHCID 152749313-Aminopyrazine-2-carbaldehyde

Produkt 1

HCID 85536480Pyrido[2,3-b]pyrazine-6,7-dicarboxylic acid, diethyl esterAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Diethyl oxalacetate, (4.7 g, 0.25 mol) and piperidine (1.66 g, 1.93 mL) are added to 3-aminopyrazine-2-carboxaldehyde (2.4 g, 0.0195 mol) dissolved in 250 mL of toluene. After the reaction mixture is refluxed for two hours, the toluene is removed under reduced pressure to give a dark red oily residue. The product is purified by column chromatography on silica gel (hexane:EtOAc, 4:1), affording 3.1 g (58% yield), of the crude desired product. Crystallization from ether-hexane (4:1) gives analytically pure compound 1.5 g (28%) having a melting point 83°-85° C.

Aufarbeitung

  1. temperatureAfter the reaction mixture is refluxed for two hours
  2. customthe toluene is removed under reduced pressure
  3. customto give a dark red oily residue
  4. customThe product is purified by column chromatography on silica gel (hexane:EtOAc, 4:1)
  5. customaffording 3.1 g (58% yield)
  6. customCrystallization from ether-hexane (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-e49dba56e1984af097348a8f47ed4d5f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622913

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