Sodium Hydroxide → [4-(Morpholin-4-ylmethyl)phenyl]methanamine

HRID 1191000

Reaktionsgleichung

Reaktionsgleichung von HRID 1191000
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH2:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[OH-].[Na+]>C1COCC1.O.C(OCC)C>[N:7]1([CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 2168644-((Morpholin-4-yl)methyl)benzonitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 2795501[4-(Morpholin-4-ylmethyl)phenyl]methanamineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under a nitrogen atmosphere, add lithium aluminum hydride (1.13 g, 29.7 mmol) to THF (50 mL) at 0° C. followed by a solution of 4-(morpholin-4-ylmethyl)-benzonitrile (2 g, 9.89 mmol) in THF (10 mL). Stir at 0° C. for 1 h and at room temperature overnight. Cool the mixture to 0° C., and carefully add water (1.15 mL). Add diethyl ether (125 mL), 3N aqueous NaOH (1.15 mL), water (3.45 mL), and stir for 1 h at room temperature. Filter the solid residue and concentrate the filtrate in vacuo to obtain the title compound as a colorless oil (1.87 g, 94%). MS (APCI+) m/z: 207 (M+H)+.

Aufarbeitung

  1. temperatureCool the mixture to 0° C.
  2. filtrationFilter the solid residue
  3. concentrationconcentrate the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-38763a18346d4bdb8e4e4c28e7e940d1
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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