(2-Nitrophenyl)(tetrahydropyran-3-yl)amine → N-(Tetrahydropyran-3-yl)benzene-1,2-diamine

Participants

Reaction Steps

A mixture of (2-nitrophenyl)(tetrahydropyran-3-yl)amine (0.72 g, 3.24 mmol) and 10% Pd/C (200 mg) in EtOAc (30 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 3 days. The suspension was then filtered through a pad of celite and the filtrate was concentrated in vacuo affording N-(Tetrahydropyran-3-yl)benzene-1,2-diamine as a colourless oil (quantitative). 1H NMR (CDCl3, 400 MHz): δ 6.80 (1H, t, J=7.55 Hz), 6.75-6.62 (3H, m), 4.00 (1H, d, J=11.24 Hz), 3.84-3.71 (1H, m), 3.67-3.16 (6H, m), 2.07-1.92 (1H, m), 1.87-1.73 (1H, m), 1.72-1.56 (2H, m).

Provenance & Evidence