3-Benzyloxyphenylacetonitrile → 2-(3-(Benzyloxy)phenyl)ethanamine

HRID 1180166

Reaktionsgleichung

Reaktionsgleichung von HRID 1180166
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][NH2:17])[CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 5198313-BenzyloxyphenylacetonitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 2074152-(3-(Benzyloxy)phenyl)ethanamineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-benzyloxyphenylacetonitrile (11.50 g, 51.50 mmol) in 100 mL of THF at 0° C. was treated with LiAlH4 (3.90 g, 103 mmol) in several portions over 20 minutes. The reaction mixture was warmed to room temperature and stirred for 30 minutes then it was heated at reflux for 6 h. The suspension was cooled to room temperature and quenched by the slow addition of Na2SO4.10H2O (25 g). The resulting mixture was diluted with 200 mL of CH2Cl2. The organic layer was separated and the remaining salt was rinsed with additional CH2Cl2 (2×50 mL). The combined organic layers were dried over MgSO4, concentrated, and purified by column chromatography (SiO2, hexanes/ethyl acetate, 2:1) to provide the title compound (5.85 g, 51% yield): ES-MS (m/z) 228 [M+H]+.

Aufarbeitung

  1. temperatureit was heated
  2. temperatureat reflux for 6 h
  3. temperatureThe suspension was cooled to room temperature
  4. customquenched by the slow addition of Na2SO4.10H2O (25 g)
  5. additionThe resulting mixture was diluted with 200 mL of CH2Cl2
  6. customThe organic layer was separated
  7. washthe remaining salt was rinsed with additional CH2Cl2 (2×50 mL)
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. concentrationconcentrated
  10. custompurified by column chromatography (SiO2, hexanes/ethyl acetate, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-641ba20e4f0f4d2e92f3d2eed19bfe85
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279489B2

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