Réaction #44017

Équation de réaction

trans-2,6-Dimethylpiperidin-4-one

trans-2,6-dimethylpiperidin-4-one

triethylamine

4-chlorobenzenesulfonyl chloride

→

product 94

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

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred for 24 hr
2. 2
   Autrepartitioned between water (300 mL) and CH2Cl2 (300 mL)
3. 3
   LavageThe organic layer was washed with 0.2 N citric acid, water, brine
4. 4
   Séchagedried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Autrethe solvent evaporated
7. 7
   AutreThe residue (6.7 g) was purified by flash chromatography
8. 8
   Lavageeluting with EtOAc-hexane (1:3) mixture

Mode opératoire

trans-2,6-Dimethylpiperidin-4-one (93; 5.2 g, 39 mmol) was dissolved in CH2Cl2 (100 mL) and triethylamine (22 mL, 155 mmol) was added. The solution was stirred and treated with 4-chlorobenzenesulfonyl chloride (9.2 g, 43 mmol). The mixture was stirred for 24 hr and then partitioned between water (300 mL) and CH2Cl2 (300 mL). The organic layer was washed with 0.2 N citric acid, water, brine, dried over Na2SO4, filtered and the solvent evaporated. The residue (6.7 g) was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture to yield 3.6 g (35%, 2 steps) of product 94.

Source