Реакция #42557

Уравнение реакции

Dimethylamine hydrochloride

4-cyano-2-bromomethylpyridine

triethylamine

→

4-cyano-2-(dimethylamino)methylpyridine

Выход 66.8%

Растворители

acetone

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture was concentrated under reduced pressure
2. 2
   Другоеpartitioned between methylene chloride and saturated sodium bicarbonate
3. 3
   ДругоеThe organic layer was separated
4. 4
   Промывкаwashed with water, saturated sodium chloride
5. 5
   Сушкаdried (sodium sulfate)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under reduced pressure
8. 8
   ДругоеPurification by flash column chromatography (silica, 99:1 methylene chloride/methanol)

Методика

Dimethylamine hydrochloride (4.78 g, 58.6 mmol) was added to a solution of 4-cyano-2-bromomethylpyridine (3.95 g, 19.5 mmol) and triethylamine (13.58 mL, 97.7 mmol) in acetone (40 mL). The reaction mixture was stirred overnight at room temperature in a sealed tube. The reaction mixture was concentrated under reduced pressure and partitioned between methylene chloride and saturated sodium bicarbonate. The organic layer was separated and washed with water, saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 99:1 methylene chloride/methanol) gave the desired 4-cyano-2-(dimethylamino)methylpyridine (2.10 g): 1H NMR (300 MHz, CDCl3) δ 8.73 (d, J=5.0 Hz, 1H), 7.71 (s, 1H), 7.41 (dd, J=5.0, 1.2 Hz, 1H), 3.65 (s, 2H), 2.31 (s, 6H); ESI MS m/z 162 [M+H]+.

Источник