تفاعل #44017

معادلة التفاعل

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

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred for 24 hr
2. 2
   أخرىpartitioned between water (300 mL) and CH2Cl2 (300 mL)
3. 3
   غسيلThe organic layer was washed with 0.2 N citric acid, water, brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvent evaporated
7. 7
   أخرىThe residue (6.7 g) was purified by flash chromatography
8. 8
   غسيلeluting with EtOAc-hexane (1:3) mixture

الإجراء التجريبي

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.

المصدر