Dimethylamine → 6-Chlorogramine

Participants

Reaction Steps

Glacial acetic acid (0,4 ml) was added dropwise to an aqueous solution at 33% (w/v) of dimethylamine (0,4 ml), cooled in an ice bath, at a speed so as not to exceed a temperature of 5° C. Under continuous stirring and in an ice bath, were added in succession an aqueous solution of formaldehyde (0,2 ml at 40% w/v) and then 420 mg of 6-chloroindole, which in approximately 10 minutes dissolved in the reaction mixture with the development of heat. The reaction mixture was left at room temperature for approximately 16 hours. The solution was then poured into NaOH 2N (10 ml) and extracted with ethyl ether (3×15 ml). The organic phase was washed with saturated NaCl/H2O (2×10 ml) and dried on anhydrous magnesium sulphate overnight. On evaporation of the solvent, a residue was obtained, of practically pure 6-chloro-gramine, equal to 550 mg (yield 95%).

Provenance & Evidence