tert-Butyl N-[4-(aminomethyl)phenyl]carbamate

Uses

Synthesis

143090-18-0

220298-96-4

General procedure for the synthesis of 4-aminomethyl-N-Boc-aniline from N-BOC-4-aminobenzonitrile: 4-(tert-butoxycarbonylamino)benzyl cyanide (1 g, 4.58 mmol) was dissolved in a solvent mixture of THF/isopropanol (1:1, 142 mL) and 10% Pd/C (Degussa type E101, 0.56 g, 0.26 mmol) was added . The reaction system was added via syringe under nitrogen protection. After purging the reaction mixture with nitrogen, it was hydrogenated overnight under 50 psi hydrogen pressure. Upon completion of the reaction, the catalyst was removed by Celite filtration. The filter cake was washed thoroughly with isopropanol (100 mL) and THF (100 mL). The filtrate was concentrated in vacuum and the resulting crude product was purified by silica gel column chromatography and separated using a methanol solution of DCM/2M ammonia (gradient elution procedure: 1:0 to 95:5 for 30 min; 95:5 for 3 min; 95:5 to 9:1 for 30 min; 9:1 for 30 min) to afford the target product, 4-aminomethyl-N-Boc-aniline (0.364 g, 36% yield) . Mass spectrum (ES-) m/z: 220.1 ([M-H]-).

References