Hydrochloric Acid → Diethyl-(2-quinoxalin-2-yl-ethyl)amine

HRID 456598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456598
Cl.[CH2:2]([NH:4][CH2:5][CH3:6])[CH3:3].[CH3:7][C:8]1[CH:17]=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[CH2:18]=O.Cl>C(O)C.O.C(N(CC)CC)C>[NH3:4].[CH2:2]([N:4]([CH2:5][CH3:6])[CH2:18][CH2:7][C:8]1[CH:17]=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:3]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 236862-MethylquinoxalineHCID 10197650Diethylammonium chloride

Produkt 2

HCID 222AmmoniaAusbeute 0,1 %HCID 17979918Diethyl-(2-quinoxalin-2-yl-ethyl)amineAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of diethylamine hydrochloride (3.82 g, 35 mmol) and triethylamine (0.23 ml) in ethanol (1.75 ml) and water (1.75 ml) was added dropwise, at 60° C., to a mixture of 2-methyl-quinoxaline (5.0 g, 35 mmol), formaldehyde (2.81 g of 37% solution, 35 mmol), triethylamine (0.17 ml) and ethanol (4.6 ml). The pH was adjusted to 7–7.5 by mean of dilute aqueous hydrochloric acid. Stirring was maintained 16 hours at 60° C. The solvent was concentrated, the residue was diluted with water and extracted with diethyl ether to remove the unreacted quinoxaline. The aqueous phase was basified with 20% aqueous sodium hydroxide (10 ml) and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with dichloromethane-methanol (first 95-5 then 90-10 and finally 90-10 plus 0.1% of ammonia) to give diethyl-(2-quinoxalin-2-yl-ethyl)-amine (2.67 g, 37%).

Aufarbeitung

  1. concentrationThe solvent was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. customto remove the unreacted quinoxaline
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with dichloromethane-methanol (first 95-5

Quellen und Nachweise

ORD-Eintrag
ord-f263539c0f034394aa574992f4747d22
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186730B2

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