Ethanol → 1-(2-Methoxyethyl)piperidine-4-carbaldehyde

HRID 1795158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795158
COC1C=C(N)C=C[C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16]O[CH2:14][CH2:13]1.[CH2:19]([OH:21])[CH3:20]>[Pd]>[CH3:8][O:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:20]([CH:19]=[O:21])[CH2:16][CH2:17]1

Komponenten

4

Edukt 2

HCID 702EthanolHCID 22185405HCID 22185405, Verbindung

Produkt 1

HCID 178939541-(2-Methoxyethyl)piperidine-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

4-[2-(2-Methoxy-4-nitro-phenoxy)-ethyl]-morpholine To a solution of (1-(2-hydroxyethyl)-morpholine) (1.94 ml, 16 mmol) in dimethylformamide was added sodium hydride [60% dispersion in oil] (544 mg, 16 mmol). After stirring at room temperature for 10 min, a solution of (1-chloro-2-methoxy-4-nitro-benzene) (3 g, 16 mmol) in dimethylformamide (10 ml) was added dropwise. The reaction mixture was left stirring at room temperature for 16 hours, concentrated, then the residue dissolved in ethyl acetate and washed with water. The organic phase was dried with magnesium sulphate, concentrated and the residue purified by column chromatography on silica gel to afford the title compound; MS(ES+) m/e 283 [M+H]+. Step 2. 3-Methoxy-4-(2-morpholin-4-yl-ethoxy)-phenylamine To a solution of the product of Step 1 (2.3 g, 8.6 mmol) in ethanol (100 ml) was added 10% palladium on charcoal (50 mg). The mixture was then stirred at room temperature under an atmosphere of hydrogen for 16 hours, filtered through celite and concentrated to give the title compound; MS(ES+) m/e 252 [M+H]+.

Aufarbeitung

  1. filtrationfiltered through celite and
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c1f4e202548643b8a6af7552c715765a
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026336B1

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