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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence