Synthesis
3-Azidomethyl-benzenecarbonitrile (12.4 g, 0.078 mol) was used as a raw material and dissolved in ethyl acetate (40 mL). To this solution was added 5% palladium-carbon catalyst (4.0 g) at room temperature and the hydrogenation reaction was carried out overnight under 45 psi hydrogen pressure. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad to remove the catalyst. Subsequently, the solvent in the filtrate was evaporated to afford 3-aminomethyl-benzenecarbonitrile as a light brown solid (7.87 g, 76% yield). The product was characterized by 1H-NMR (CDCl3): δ 7.62-7.57 (m, 1H), 7.56-7.43 (m, 2H), 7.42-7.31 (m, 1H), 3.87 (s, 2H).
References
[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1067 - 1088
[2] Patent: WO2016/7966, 2016, A2. Location in patent: Paragraph 0031
[3] Patent: US2006/94749, 2006, A1. Location in patent: Page/Page column 11
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3477 - 3482
