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

HRID 51837

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9787000faa6f4ac79af27da87f73a7f1
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713499B2

Linked notes

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