Réaction #61042

Équation de réaction

Trans-1,2-diaminocyclohexane

(2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

pyrazole

potassium carbonate

→

title compound

Rendement 21.0%

(5-Methanesulfonyl-2-pyrazol-1-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Rendement 21.0%

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   Autrequenched with water/dichloromethane
3. 3
   ExtractionThe aqueous layer was extracted twice with dichloromethane
4. 4
   Séchagedried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Autrethe solvent was removed in vacuo
7. 7
   AutreThe crude oil was chromatographed over silicagel

Mode opératoire

In a tube were added successively (2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (compound CK, 0.1 g, 0.19 mmol), pyrazole (15 mg, 0.223 mmol), potassium carbonate (51 mg, 0.37 mmol), CuI (7 mg, 0.037 mmol), Trans-1,2-diaminocyclohexane (9 ul, 0.07 mmol) and dioxane (0.4 ml). The mixture was heated under argon at 120° C. for 24 hours. The reaction mixture was cooled to room temperature and quenched with water/dichloromethane. The aqueous layer was extracted twice with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silicagel: eluent: heptane/ethylacetate: 0-5% to provide the title compound as a light grey powder (19 mg, 21%), MS (m/e): 479.1 (M+H, 100%)

Source