Reaction #1929063

Reaction equation

6-(2-cyan-acetylamino)hexanoic acid

3-dimethylamino-4-methoxybenzaldehyde

piperidine

→

6-[2-cyan-3-(3-dimethylamino-4-methoxy-phenyl)acryloylamino]hexanoic acid

Solvents

pyridine

Conditions

Workup

1. 1
   OtherAfter evaporation of the reaction mixture the residue
2. 2
   ExtractionThe aqueous phase was extracted with ethyl acetate
3. 3
   WashThe collected ethyl acetate phases were washed with NaCl-Solution
4. 4
   Otherdried
5. 5
   Otherevaporated
6. 6
   OtherThe residue was chromatographed on SiO2 with ethyl acetate under low pressure
7. 7
   OtherThe product was crystallized from little ethyl acetate

Procedure

3.96 g (20 mMol 6-(2-cyan-acetylamino)hexanoic acid was dissolved in 27 ml pyridine. 3.64 g (20 mMol) 3-dimethylamino-4-methoxybenzaldehyde and 0.6 mL piperidine were added to the solution and the reaction mixture was stirred for 20 hours. After evaporation of the reaction mixture the residue was solved in 150 ml ethyl acetate and 150 ml water and the pH was adjusted with pure acetic acid to 4.2. The aqueous phase was extracted with ethyl acetate. The collected ethyl acetate phases were washed with NaCl-Solution, dried and evaporated. The residue was chromatographed on SiO2 with ethyl acetate under low pressure. The product was crystallized from little ethyl acetate.

Source