1-(4-(AMinoMethyl)phenyl)-N,N-diMethylMethanaMine hydrochloride

Synthesis

General procedure for the synthesis of 1-(4-(aminomethyl)phenyl)-N,N-dimethylmethylamine hydrochloride from 4-[(dimethylamino)methyl]benzonitrile: To a solution of 4-[(dimethylamino)methyl]benzonitrile (1.30 g, 8.12 mmol, 1.0 eq.) in tetrahydrofuran (THF, 10 mL), was added 1 M borane-tetrahydrofuran complex ( 24.4 mL, 24.4 mmol, 3.0 equiv). The reaction mixture was heated to reflux temperature and kept under nitrogen protection for 16 hours. After completion of the reaction, it was cooled to room temperature, a methanol solution of 1 M hydrochloric acid (20 mL) was added and heated to reflux again for 1 hour. After the reaction mixture was cooled to room temperature, the precipitate was collected by filtration. The resulting solid was washed with ether and dried in vacuum to give 1-(4-(aminomethyl)phenyl)-N,N-dimethylmethylamine hydrochloride (1.50 g, 7.50 mmol, 92.6% yield) as a white solid.

References

[1] Patent: WO2016/144792, 2016, A1. Location in patent: Paragraph 00900; 00902
[2] Patent: US2004/10033, 2004, A1. Location in patent: Page/Page column 22-23
[3] Patent: EP1105120, 2005, B1. Location in patent: Page/Page column 25