1,1-Dicyanocyclopentane → 1,1-Cyclopentanedimethanamine

HRID 12479

Reaktionsgleichung

Reaktionsgleichung von HRID 12479
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:14]#[N:15])([C:12]#[N:13])[CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[NH2:13][CH2:12][C:7]1([CH2:14][NH2:15])[CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

4

Edukt 2

HCID 151720351,1-DicyanocyclopentaneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 4325931,1-Cyclopentanedimethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A suspension of LiAlH4 (4.74 g) in dry Et2O (100 mL) was cooled in an ice bath, and a solution of cyclopentane-1,1-dicarbonitrile (5.0 g) in Et2O (50 mL) was added dropwise at such a rate that the temperature was kept below 20° C. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness under reduced pressure to give 4.95 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 1.24 (br s, 4H), 1.22-1.40 (m, 4H), 1.55-1.64 (m, 4H), 2.62 (s, 4H).

Aufarbeitung

  1. temperaturewas cooled in an ice bath
  2. customwas kept below 20° C
  3. temperaturecooled in an ice bath
  4. customquenched
  5. additionby adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL)
  6. filtrationThe suspension was filtered
  7. washthe filter cake was washed with Et2O
  8. customthe combined filtrates were evaporated to dryness under reduced pressure
  9. customto give 4.95 g of a clear, colorless liquid

Quellen und Nachweise

ORD-Eintrag
ord-1fe459bff36d43cdb7b880e57236a9c8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728018B2

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