N-Methyl-4-anisidine → 4-methoxy-N-(2-methoxyethyl)-N-methylaniline

HRID 51837

Reaktionsgleichung

Reaktionsgleichung von HRID 51837
[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[CH3:20][O:21][CH2:22][CH2:23]Br>C(#N)C>[CH3:20][O:21][CH2:22][CH2:23][N:2]([C:3]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[CH:5][CH:4]=1)[CH3:1]

Komponenten

5

Edukt 3

HCID 22250N-Methyl-4-anisidineHCID 809722-Bromoethyl methyl etherHCID 81531Diisopropylethylamine

Produkt 1

HCID 118437404-methoxy-N-(2-methoxyethyl)-N-methylanilineAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 1.00 g (7.29 mmol) N-methyl-p-anisidine in 15 ml acetonitrile at 0° C. were added dropwise 1.36 ml (8.02 mmol) N-ethyldiisopropylamine and 1.01 g (7.29 mmol) 2-bromoethyl methyl ether. The mixture was heated at 80° C. for 2 days and then concentrated in vacuo. Flash chromatography (1/9 ethyl acetate/hexane) afforded 1.20 g (84%) (2-methoxy-ethyl)-(4-methoxy-phenyl)-methyl-amine as an orange oil. ES-MS m/e (%): 196 (M+H+, 100).

Aufarbeitung

  1. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9787000faa6f4ac79af27da87f73a7f1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713499B2

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