Reaction #46243

Reaction equation

[6-(4-cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester

→

[6-(4-aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Solvents

EtOH

NH3.H2O

Conditions

Workup

1. 1
   FiltrationThe catalyst was filtered off
2. 2
   Concentrationthe filtrate was concentrated to dryness

Procedure

A suspension of [6-(4-cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester (7.0 g, 24 mmol), Raney Ni (1.0 g) in EtOH (500 mL) and NH3.H2O (10 mL) was hydrogenated under H2 (50 psi.) at 50° C. for 6 h. The catalyst was filtered off and the filtrate was concentrated to dryness to give [6-(4-aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid tert-butyl ester, which was used directly in next step. 1H NMR (300 MHz, CDCl3) δ 7.83-7.92 (m, 3H), 7.70 (t, J=7.8 Hz, 1H), 7.33-7.40 (m, 4H), 3.92 (brs, 2H), 1.53 (s, 9H).

Source