Réaction #61165

Équation de réaction

1-(5-chloro-2-nitro-phenyl)-piperidine

NaOMe

MeOH

→

title compound

Rendement 41.0%

1-(5-Methoxy-2-nitro-phenyl)-piperidine

Rendement 41.0%

Solvants

EtOAc

DMF

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (50 mL)
2. 2
   Séchagedried (Na2SO4)
3. 3
   Concentrationconcentrated in vacuo
4. 4
   AutrePurification by preparative TLC (20% EtOAc-hexane)

Mode opératoire

To 1-(5-chloro-2-nitro-phenyl)-piperidine (197 mg, 0.810 mmol) in 1.5 mL of DMF was added 4 mL of 0.5 M NaOMe in MeOH (2.5 eq). The resultant solution was heated at 60° C. overnight, then at 90° C. for 24 h. The reaction was diluted with EtOAc (50 mL) and washed with water (50 mL), dried (Na2SO4) and concentrated in vacuo. Purification by preparative TLC (20% EtOAc-hexane) gave 80 mg (41%) of the title compound, along with 80 mg (40%) of recovered starting material. 1H-NMR (CDCl3; 400 MHz): δ 7.95 (d, 1H, J=9.1 Hz), 6.51 (d, 1H, J=2.6 Hz), 6.46 (dd, 1H, J=2.6, 9.1 Hz), 3.87 (s, 3H), 3.01-3.04 (m, 4H), 1.72-1.78 (m, 4H), 1.60-1.64 (m, 2H).

Source