Réaction #44015

Équation de réaction

water

triethylamine

cis-2,6-dimethylpiperidin-4-one

4-chlorobenzenesulfonyl chloride

→

cis-1-(4-chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   LavageOrganic layer was washed with 0.2 N citric acid, water, brine
2. 2
   Séchagedried over anhydrous Na2SO4
3. 3
   FiltrationThe solution was filtered
4. 4
   Autreevaporated
5. 5
   AutreThe residue was purified by flash chromatography
6. 6
   Lavageeluting with EtOAc-hexane (1:3) mixture

Mode opératoire

The crude cis-2,6-dimethylpiperidin-4-one 91 from previous experiment (1.1 g, 8.6 mmol) was dissolved in CH2Cl2 (50 mL) and triethylamine (5 mL, 35 mmol) was added. Stirred solution was treated with 4-chlorobenzenesulfonyl chloride (2.2 g, 9.5 mmol). The mixture was stirred for 24 hr then was divided between water (100 mL) and CH2Cl2 (100 mL). Organic layer was washed with 0.2 N citric acid, water, brine and dried over anhydrous Na2SO4. The solution was filtered and evaporated. The residue was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture. Yield 60 mg (2% after two steps).

Source