Réaction #61169

Équation de réaction

1-(5-imidazol-1-yl-2-nitro-phenyl)-piperidine

→

title compound

Rendement 66.0%

4-Imidazol-1-yl-2-piperidin-1-yl-phenylamine

Rendement 66.0%

Solvants

THF

H2O

Conditions de réaction

Traitement

1. 1
   Extractionthe reaction was extracted with 20 mL of EtOAc
2. 2
   Extractionextracted with EtOAc (3×20 mL)
3. 3
   LavageThe combined organic layers were washed with brine (20 mL)
4. 4
   Séchagedried (Na2SO4)
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

To 1-(5-imidazol-1-yl-2-nitro-phenyl)-piperidine (117 mg, 0.430 mmol, as prepared in the previous step) in 3 mL of THF was added 6.5 mL of 10% TiCl3 in H2O dropwise over 3 min. After 10 min, the reaction was extracted with 20 mL of EtOAc, and the organic layer was discarded. The aqueous layer was basified with 10M NaOH to pH>9, then extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), and concentrated in vacuo to afford 74 mg (66%) of the title compound as a light brown solid. Mass spectrum (ESI, m/z): Calcd. for C14H18N4, 243.1 (M+H), found 243.2;

Source