Diethyl Ether → 3-Cyclopropyl-4-methoxybenzenemethanamine

HRID 1675952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1675952
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH:12]1([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:18]#[N:19])[CH2:14][CH2:13]1>O1CCCC1>[CH:12]1([C:15]2[CH:16]=[C:17]([CH2:18][NH2:19])[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 574847073-Cyclopropyl-4-methoxybenzonitrile

Produkt 1

HCID 591873703-Cyclopropyl-4-methoxybenzenemethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminum hydride in diethyl ether (17.3 ml, 1.0 M, 17.3 mmol, 3.0 eq) was carefully added over twenty minutes to a solution of 3-cyclopropyl-4-methoxybenzonitrile (8-2, 1.0 g, 5.77 mmol, 1.0 eq) in tetrahydrofuran (28.9 ml) at 0° C. under nitrogen atmosphere. The resulting dark orange mixture was allowed to stir at 0° C. for 30 min, then carefully quenched in the following order: water (1.0 ml), 15% NaOH aqueous (1.0 ml) and water (3.0 ml). The resulting emulsion was stirred at room temperature for 30 min. Several spatula amounts of magnesium sulfate was added to the mixture to remove any water. The entire mixture was filtered through a pad of sodium sulfate, washing with ethyl acetate. The collected filtrate was concentrated to give the product (8-3) as a yellow oil. ESI+MS [M-16]+ C11H15NO: 161.1 found, 161.2 required.

Aufarbeitung

  1. customcarefully quenched in the following order
  2. stirringThe resulting emulsion was stirred at room temperature for 30 min
  3. additionSeveral spatula amounts of magnesium sulfate was added to the mixture
  4. customto remove any water
  5. filtrationThe entire mixture was filtered through a pad of sodium sulfate
  6. washwashing with ethyl acetate
  7. concentrationThe collected filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-5a98ff18569945ea8b721645be8089df
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003797B2

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