Реакция #58482

Уравнение реакции

n-butyl lithium

2-dimethylamino-ethanol

2-chloropyridine

1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide

→

title product

Выход 47.6%

2-Chloro-6-(1-methylpiperidin-4-ylcarbonyl) pyridine

Выход 47.6%

Растворители

hexane

hexane

Условия реакции

Обработка

1. 1
   ДругоеQuench the reaction mixture with water
2. 2
   Экстракцияextract twice with ethyl acetate
3. 3
   Сушкаdry the organic layer with anhydrous sodium sulfate
4. 4
   Другоеevaporate the solvent
5. 5
   Другоеpurify the residual product by chromatography on a silica gel column

Методика

Add 2-chloropyridine (1 g, 8.8 mmole) to a mixture of n-butyl lithium (1.6 M in hexane) (22 mL, 35.2 mmole) and 2-dimethylamino-ethanol (1.56 g, 17.6 mmole) in hexane (20 mL at −78° C.) and stirred for 1 hour. Then add 1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide (3.2 g, 17.6 mmole) in hexane (5 mL) and stir the mixture for 1 hour. Quench the reaction mixture with water and extract twice with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, evaporate the solvent and purify the residual product by chromatography on a silica gel column to give about 1 g of the title product.

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