Dimethylamine → HCID 86752483, compound

Participants

Reaction Steps

Dimethylamine (3.35 ml of 33% solution in methylated spirit) was added to astirred mixture of benzyl (E)-3-(2-methyl-1H-indol-5-yl)-2-propenoate (6.50g) in a mixture of acetic acid (14 ml) and tetrahydrofuran (15 ml) at 0° C., followed by the dropwise addition of formaldehyde (1.75 ml of 40% aqueous solution). The mixture was stirred at room temperature for 3 hours and then diluted with ethyl acetate. 2N sodium hydroxide was addeddropwise with stirring until the pH of the aqueous layer was ca.9. The mixture was filtered, and the residue was washed with water followed by ethyl acetate and then dried to give the title compound (6.58 g), m.p. 174°-177° C. Found: C,75.85; H,6.83; N,7.53. C22 H24N2O2 requires: C,75.83; H,6.94; N,8.04%.

Provenance & Evidence