Triethylamine → 4-Cyano-2-(dimethylamino)methylpyridine

Reaction equation

Cl.[CH3:2][NH:3][CH3:4].[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13]Br)[CH:8]=1)#[N:6].C(N(CC)CC)C>CC(C)=O>[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][N:3]([CH3:4])[CH3:2])[CH:8]=1)#[N:6]

Participants

Procedure

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]+.