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ChemicalBook CAS DataBase List N-[(4-methoxyphenyl)methyl]-4-methylaniline
112825-69-1

N-[(4-methoxyphenyl)methyl]-4-methylaniline synthesis

9synthesis methods
-

Yield: 70%

Reaction Conditions:

Stage #1:C15H19NO2 with 4-nitro-benzoic acid in acetonitrile at 80; for 10 h;Inert atmosphere;
Stage #2: with sodium carbonate in acetonitrileInert atmosphere;regioselective reaction;

Steps:

General experimantal procedure for the synthesis of aryl amines:
General procedure: In a srew capped 5.0 ml vessel, a mixture of aziridine (0.50 mmol) and p-NBA (0.38 mmol) in 1.0 ml of acetonitrile was heated at 80 oC for desired time under argon. After complete reaction (TLC), 5.0 ml concentrated solution of sodiumcarbonate was added and stirred for few minutes. The solution was extracted with ethylacetate (20.0 x 2 ml) and washed with brine. Evaporation of the organic layer followed by small silica gel column chromatography (eluted with hexanes/ethylacetate) to afford pure desired product.

References:

Barros, M. Teresa;Dey, Suvendu S.;Maycock, Christopher D.;Rodrigues, Paula [Tetrahedron,2012,vol. 68,# 31,p. 6263 - 6268] Location in patent:supporting information; experimental part