تفاعل #42557

معادلة التفاعل

Dimethylamine hydrochloride

4-cyano-2-bromomethylpyridine

triethylamine

→

4-cyano-2-(dimethylamino)methylpyridine

المردود 66.8%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was concentrated under reduced pressure
2. 2
   أخرىpartitioned between methylene chloride and saturated sodium bicarbonate
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with water, saturated sodium chloride
5. 5
   تجفيفdried (sodium sulfate)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىPurification by flash column chromatography (silica, 99:1 methylene chloride/methanol)

الإجراء التجريبي

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]+.

المصدر