Diethyl[2-(4-nitrophenoxy)ethyl]amine → 4-(2-(Diethylamino)ethoxy)aniline

Participants

Reaction Steps

To a solution of diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine 2 (14.0 mmol) in MeOH (20 mL), in a Parr pressure bottle, is added Pd (10% on carbon, 50% wet, 10% weight). The suspension is shaken at 50 psi of H2 for 2 h. The reaction mixture is filtered through celite. The solvent is removed and the residue is dissolved in MeOH (20 mL) and treated with HCl (1 eq of a 4N solution in dioxane) to afford 4-(2-diethylamino-ethoxy)-phenylamine 3 as hydrochloride salt. 1H NMR (400 MHz, d6-DMSO) δ 6.98-6.91 (m, 4H), 4.30 (t, J=4.0 Hz, 2H), 3.47 (t, J=4.0 Hz), 3.20 (m, 4H), 1.24 (t, J=8.0 Hz, 6H). MS (m/z) (M+1)+: 209.3.

Provenance & Evidence