Reaktion #42557

Reaktionsgleichung

Dimethylamine hydrochloride

4-cyano-2-bromomethylpyridine

triethylamine

→

4-cyano-2-(dimethylamino)methylpyridine

Ausbeute 66.8%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under reduced pressure
2. 2
   Sonstigepartitioned between methylene chloride and saturated sodium bicarbonate
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with water, saturated sodium chloride
5. 5
   Trocknendried (sodium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigePurification by flash column chromatography (silica, 99:1 methylene chloride/methanol)

Vorschrift

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]+.

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