Triethylamine → Eproxindine

Participants

Reaction Steps

15 g of 2-chloro-N-methyl-pyridinium iodide in 150 ml of methylene chloride and 14 ml of triethylamine are added to 13.3 g of N-phenyl-3-methoxyindole-2-carboxylic acid, dissolved in 100 ml of methylene chloride. After one hour at room temperature, 5.5 g of 3-amino-1,2-propanediol in 50 ml of pyridine are added and the reaction solution is stirred overnight. It is then evaporated, the residue is taken up in methylene chloride and the mixture is washed successively with dilute hydrochloric acid, dilute sodium hydroxide solution and saturated sodium chloride solution. After the organic phase has been dried and evaporated, the oil which remains is taken up in ethyl acetate and recrystallised. Yield: 8.1 g of

Provenance & Evidence