1,1-Cyclohexanedicarbonitrile → [1-(Aminomethyl)cyclohexyl]methanamine

HRID 12482

Reaktionsgleichung

Reaktionsgleichung von HRID 12482
[C:1]1([C:9]#[N:10])([C:7]#[N:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH2:8][CH2:7][C:1]1([CH2:9][NH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 5445611,1-CyclohexanedicarbonitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 71994[1-(Aminomethyl)cyclohexyl]methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Cyclohexane-1,1-dicarbonitrile (20.0 g) was taken up in dry Et2 (70 mL). This mixture was added dropwise to a suspension of LiAlH4 (17.0 g) in dry Et2O (250 mL) cooled in an ice bath. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (17.0 mL), 2M aqueous NaOH (34.0 mL) and again H2O (17 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness yielding 20.8 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 1.05-1.55 (m, 14H), 2.61 (s, 4H).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. temperaturecooled in an ice bath
  3. customquenched
  4. additionby adding H2O (17.0 mL), 2M aqueous NaOH (34.0 mL) and again H2O (17 mL)
  5. filtrationThe suspension was filtered
  6. washthe filter cake was washed with Et2O
  7. customthe combined filtrates were evaporated to dryness
  8. customyielding 20.8 g of a clear, colorless liquid

Quellen und Nachweise

ORD-Eintrag
ord-fb00120b424c46bd9458335a138b45b6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728018B2

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