4-((Morpholin-4-yl)methyl)benzonitrile → [4-(Morpholin-4-ylmethyl)phenyl]methanamine

HRID 1181440

Reaktionsgleichung

Reaktionsgleichung von HRID 1181440
[N:1]1([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:1]1([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 2168644-((Morpholin-4-yl)methyl)benzonitrileHCID 21226445Aluminium lithium hydride2×

Produkt 1

HCID 2795501[4-(Morpholin-4-ylmethyl)phenyl]methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 4-(morpholin-4-ylmethyl)benzonitrile (Description 122, 0.5 g, 2.5 mmol) in THF (7 mL) at 0° C. was added dropwise a solution of LiAlH4 (1.0 M in THF, 2.5 ml, 2.5 mmol). The reaction was stirred at 0° C. for 1 h. Additional LiAlH4 (1.0 M in THF, 1.0 ml, 1.0 mmol) was added and the reaction stirred for an additional 30 min. The reaction was quenched by the addition of water (0.13 mL) followed by 15% NaOH solution (0.13 ml) and stirred vigorously for 1 h. The reaction was filtered through celite, evaporated and azeotroped twice with toluene. The amine was used crude.

Aufarbeitung

  1. stirringthe reaction stirred for an additional 30 min
  2. customThe reaction was quenched by the addition of water (0.13 mL)
  3. stirringstirred vigorously for 1 h
  4. filtrationThe reaction was filtered through celite
  5. customevaporated
  6. customazeotroped twice with toluene

Quellen und Nachweise

ORD-Eintrag
ord-8a0957426ebb42bcad5ce42afc2acd71
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285563B2

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