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Ethylenediamine → N-[1-(1-methyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamine

HRID 420850
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 420850
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=O)[CH3:8])[CH:4]=[N:3]1.[CH2:10]([NH2:13])[CH2:11][NH2:12].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.O1CCCC1.C(O)(=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]([NH:12][CH2:11][CH2:10][NH2:13])[CH3:8])[CH:4]=[N:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 3301EthylenediamineHCID 516892Sodium BicarbonateHCID 35969391-(1-methyl-1H-pyrazol-4-yl)ethan-1-oneHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 14009898N-[1-(1-methyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamineAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176
Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(1-Methyl-1H-pyrazol-4-yl)-ethanone (250 mg) and ethylenediamine (362 mg) were dissolved in methanol (10 ml), the solution was added with acetic acid (1.21 g) and sodium cyanoborohydride (189 mg), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and tetrahydrofuran, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1) to obtain the title compound (163 mg).

Aufarbeitung

  1. customthe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-c448b2dc18304b66a020f37dce9cbb5a
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08097708B2

Notizen zur Reaktion

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