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

HRID 14279Notes

Reaction equation

HRID 14279 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

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 210859452-(Bromomethyl)pyridine-4-carbonitrile

Product 1

HCID 204987244-Cyano-2-(dimethylamino)methylpyridineYield 66.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between methylene chloride and saturated sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with water, saturated sodium chloride
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (silica, 99:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-3488273b8c744aab824016f87926931d
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

Loading…