Diethyl Ether → 2-Cyclopropyl-2-phenylethan-1-amine

HRID 1243275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243275
[C:1]1([C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:18](OCC)C>>[CH:9]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:10][NH2:11])[CH2:8][CH2:18]1

Komponenten

4

Edukt 3

HCID 3283Diethyl EtherHCID 702881-PhenylcyclopropanecarbonitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 159197562-Cyclopropyl-2-phenylethan-1-amine

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Phenyl-1-cyclopropanecarbonitrile (1.0 g, 6.98 mmol) was added to a stirred suspension of lithium aluminum hydride in anhydrous diethyl ether (25 mL). The suspension was refluxed for 2 h, then cooled to 0° C., and the excess hydride was destroyed by careful addition of water. After treatment with sodium hydroxide (1 N), the mixture was filtered and the filtrate extracted with diethyl ether. After drying of the organic phase with and evaporation 2 (719 mg, 70% ) was obtained as a clear liquid and used without further purification. 1H NMR (DMSO-d6): δ 7.28 (m, 4 H), 7.17 (m, 1 H), 2.70 (s, 2 H), 1.45 (bs, 2 H); 0.78 (dd, J=6.2, 3.8 Hz, 2 H); 0.67 (dd, J=6.2 Hz, 3.8 Hz, 2 H). MS: (m/z) 148 (M+1)+.

Aufarbeitung

  1. temperatureThe suspension was refluxed for 2 h
  2. customthe excess hydride was destroyed by careful addition of water
  3. filtrationAfter treatment with sodium hydroxide (1 N), the mixture was filtered
  4. extractionthe filtrate extracted with diethyl ether
  5. customAfter drying of the organic phase with and
  6. customevaporation 2 (719 mg, 70% )
  7. customwas obtained as a clear liquid
  8. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a21da4ec57824f7fb82a2885de565d9a
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119073B2

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