Reacción #42557

Ecuación de reacción

Dimethylamine hydrochloride

4-cyano-2-bromomethylpyridine

triethylamine

→

4-cyano-2-(dimethylamino)methylpyridine

Rendimiento 66.8%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
2. 2
   Otropartitioned between methylene chloride and saturated sodium bicarbonate
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with water, saturated sodium chloride
5. 5
   Secadodried (sodium sulfate)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroPurification by flash column chromatography (silica, 99:1 methylene chloride/methanol)

Procedimiento

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]+.

Fuente