Реакция #44017

Уравнение реакции

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

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred for 24 hr
2. 2
   Другоеpartitioned between water (300 mL) and CH2Cl2 (300 mL)
3. 3
   ПромывкаThe organic layer was washed with 0.2 N citric acid, water, brine
4. 4
   Сушкаdried over Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Другоеthe solvent evaporated
7. 7
   ДругоеThe residue (6.7 g) was purified by flash chromatography
8. 8
   Промывкаeluting with EtOAc-hexane (1:3) mixture

Методика

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.

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