Réaction #60974

Équation de réaction

(5-Amino-2-morpholin-4-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

triethylorthoformate

sodium azide

→

title compound

Rendement 52.0%

(2-Morpholin-4-yl-5-tetrazol-1-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Rendement 52.0%

Solvants

Acetic acid

water

NaOH

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   ExtractionThe aqueous phase was extracted with ethyl acetate
3. 3
   Séchagedried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated to dryness
6. 6
   AutreThe residue was chromatographed on silica gel

Mode opératoire

A suspension of (5-Amino-2-morpholin-4-yl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (50 mg, 0.115 mmol) in Acetic acid (1 ml) was heated to 75° C. under nitrogen and then triethylorthoformate (36.76 ul, 0.34 mmol) was slowly added. After 1 hour, sodium azide (22.4 mg, 0.34 mmol) was added portionwise and the reaction mixture was stirred at 75° C. for 1 h 30. The reaction mixture was cooled to room temperature, diluted with water and basified with 1N NaOH solution. The aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed on silica gel: Eluent: Heptane/Ethylacetate 0% to 60% (10 minutes) to provide the title compound (29 mg, 52%) as yellow solid, MS (m/e): 488.2 (M+H+, 100%)

Source