1-(4-Nitrobenzyl)pyrrolidine → 4-(Pyrrolidin-1-ylmethyl)aniline

Participants

Reaction Steps

10% Pd/C (500 mg) was added to a solution of 1-(4-nitrobenzyl)-pyrrolidine Compound 1n3 (4.56 g, 22.1 mmol) in EtOAc (20 mL). The mixture was hydrogenated at 50 PSI for a period of 2 hrs and filtered through Celite. The filtrate was evaporated and the residue was dissolved in 10% NH4Cl and washed with ethyl ether. The aqueous layer was then adjusted to pH 10 with NaOH and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and evaporated in vacuo to give 4-pyrrolidin-1-ylmethyl-phenylamine Compound 1n (3.05 g) as a light brown oil. 1H NMR (CDCl3) δ 7.10 (d, J=8.5 Hz, 2H); 6.63 (d, J=8.5 Hz, 2H); 3.60 (br s, 2H); 3.50 (s, 2H); 2.52-2.42 (m, 4H); 1.83-1.69 (m, 4H).

Provenance & Evidence