Ammonium Hydroxide → 2-[4-(1-Aminoethyl)-3-methylphenyl]-2-methylpropanenitrile

Participants

Reaction Steps

To a stirred solution of 2-(4-acetyl-3-methylphenyl)-2-methylpropanenitrile (1.0 g, 4.97 mmol) in 7 M ammonia in MeOH (40 mL) is added titanium (IV) isopropoxide (3.0 g, 9.95 mmol). The reaction mixture is left stirring 24 h at room temperature. After cooling to 0° C., sodium borohydride (1.0 g, 19.9 mmol) is added and the reaction mixture stirred and left to warm-up to room temperature 1 h. Conc. ammonium hydroxide (15 mL) is then added and the titanium oxide is removed by filtration and is washed with ethyl acetate. The filtrate is extracted with EtOAc (2×100 mL) and the combined organic layers are dried over MgSO4, filtered and concentrated under reduced to provide the expected product 2-[4-(1-aminoethyl)-3-methylphenyl]-2 methylpropanenitrile (1.0 g, 99%) as a clear yellow oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.33 (d, J=6.64 Hz, 3H) 1.44 (s, 2H) 1.70 (s, 6H) 2.36 (s, 3H) 4.34 (q, J=6.44 Hz, 1H) 7.22 (d, J=1.95 Hz, 1H) 7.28 (dd, J=8.20, 2.15 Hz, 1H) 7.48 (d, J=8.20 Hz, 1H)

Provenance & Evidence