Triethylamine → 2-(pyridin-3-yl)acetamide

Temperature

0 °C

A solution of 3-pyridylacetic acid hydrochloride (2.6 g), triethylamine (1.52 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.16 g) and N-hydroxybenzotriazole (2.52 g) in N,N-dimethylformamide (40 ml) was stirred at 0° C. for 15 minutes. (2E,4E)- and (2Z,4E)-4-Methyl-2,4-heptadien-1-ylamine (2.69 g) was added to the solution. The solution was stirred at 0° C. for 2 hours and then at room temperature overnight. The reaction mixture was evaporated in vacuo and the residue was diluted with ethyl acetate and washed with aqueous sodium hydrogen carbonate solution. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (4% methanol-chloroform) to give N-[(2E,4E)- and (2Z,4E)-4-methyl-2,4-heptadien-1-yl]-3-pyridylacetamide (3.19 g) as an oil.

1. customat room temperature
2. customovernight
3. customThe reaction mixture was evaporated in vacuo
4. additionthe residue was diluted with ethyl acetate
5. washwashed with aqueous sodium hydrogen carbonate solution
6. washThe organic layer was washed with water and brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customevaporated in vacuo
9. customThe residue was chromatographed on silica gel (4% methanol-chloroform)

ORD record

ord-9b914bdf2e9f4d518411cd473b23b8cc

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05691366