BENZYL-(3,4,5-TRIMETHOXY-BENZYL)-AMINE synthesis

6synthesis methods

Product Name:BENZYL-(3,4,5-TRIMETHOXY-BENZYL)-AMINE
CAS Number:94271-52-0
Molecular formula:C17H21NO3
Molecular Weight:287.35

Benzenemethanamine, N-[(3,4,5-trimethoxyphenyl)methylene]-

189245-78-1
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94271-52-0
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Yield:94271-52-0 271 mg

Reaction Conditions:

with sodium tetrahydroborate in methanol at 20; for 0.583333 h;

Steps:

General procedure for the synthesis of secondary benzylamines 1d-n

General procedure: A mixture of primary amine (1 mmol) and the corresponding aldehyde (1 mmol) was heated in an oil bath at 120 °C for 20-45 min. After complete disappearance of the starting materials, as monitored by thin-layer chromatography (TLC), the mixture was allowed to cool at ambient temperature and dissolved in methanol (4-5 mL). Then, solid NaBH₄ (2.0 mmol) was added portion-wise with stirring over a period of 5 min. The stirring was continued at ambient temperature for 30 min further. After the reaction was complete (monitored by TLC), the volume of the reaction mixture was reduced to 1 mL under reduced pressure, and water (5 mL) was added. The aqueous solution was extracted with ethyl acetate (5 mL x 2), and the combined organic extracts were dried with anhydrous Na₂SO₄. The mixture was filtered and the solvent was removed under reduced pressure. All products were used without further purification. Analytical and spectroscopic data for these amines are reported in the Supplementary Material.

References:

Abonia, Rodrigo;Castillo, Juan C.;Garay, Alexander;Insuasty, Braulio;Quiroga, Jairo;Nogueras, Manuel;Cobo, Justo;D'Vries, Richard [Tetrahedron Letters,2017,vol. 58,# 15,p. 1490 - 1494] Location in patent:supporting information

86-81-7 Synthesis