Uses
3-Thiophenemethylamineis an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.
Synthesis
General procedure for the synthesis of 3-aminomethylthiophene from 3-cyanothiophene: Ruthenium(II) complex (1 M) and 2-butanol (5 mL) were added to a 25 mL flask under argon protection and stirred for 5 min at room temperature. Subsequently, KOtBu (0.05 mM) was added and stirring was continued for 5 minutes. Next, 3-cyanothiophene (0.5 mM) was added and the reaction mixture was heated on a hot plate at 120°C for 30 minutes. Upon completion of the reaction, the catalyst was removed by addition of petroleum ether followed by filtration. The filtrate was neutralized with 1 M HCl. The ether layer was purified by short path silica gel column chromatography. Hexadecane was added to the purified filtrate as an internal standard and the yield of the product 3-aminomethylthiophene was determined by gas chromatography (GC).
References
[1] Organic Process Research and Development, 2012, vol. 16, # 1, p. 109 - 116
[2] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4991 - 5002
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14653 - 14657
[4] Angew. Chem., 2016, vol. 128, # 47, p. 14873 - 14877,5
[5] Journal of Coordination Chemistry, 2015, vol. 68, # 2, p. 321 - 334
