1-(2-Fluoroethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine → 4-[1-(2-Fluoroethyl)-4-piperidinyl]-2-(methyloxy)aniline

Participants

Reaction Steps

To 1-(2-fluoroethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (0.90 g, 3.2 mmol) in EtOAc (20 mL) was added Pd (10%) on carbon (100 mg). The reaction was evacuated then refilled with 10 psi H2 gas. The reaction was stirred for 3 days. The reaction was evacuated and the atmosphere replaced with N2. The solution was filtered to remove Pd/carbon and rotovaped down to give the title compound of step C as a red crystalline solid (800 mg, 3.2 mmol, 100% yield). 1H NMR (400 MHz, CDCl3) δ 6.69 (s, 1H), 6.66-6.64 (m, 2H), 4.70 (dd, J=5.1, 4.8 Hz, 1H), 4.58 (dd, J=5.1, 4.81 Hz, 1H), 3.83 (s, 3H), 3.69 (brs, 2H), 3.17-3.05 (m, 2H), 2.84-2.72 (m, 2H), 2.48-2.36 (m, 1H), 2.27-2.14 (m, 2H), 1.92-1.79 (m, 4H).

Provenance & Evidence