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

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

9synthesis methods

Product Name:N-[(4-methoxyphenyl)methyl]-4-methylaniline
CAS Number:112825-69-1
Molecular formula:C15H17NO
Molecular Weight:227.3

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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N-[(4-methoxyphenyl)methyl]-4-methylaniline

112825-69-1
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$57.00/250mg

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