Dimethylamine → 6-Chlorogramine

Participants

Reaction Steps

The starting material is prepared as follows: To the solution of 265 ml of acetic acid, 116 ml of 36% aqueous formaldehyde and 190 ml of 40% aqueous dimethylamine, 226.5 g of 6-chloroindole are added portionwise during 45 minutes while stirring at about 40°. The mixture is heated to 60° for 15 minutes and stirred at room temperature for 1 hour. It is cooled to 10°, combined with 500 ml of water, 400 ml of 25% aqueous sodium hydroxide and 100 ml of 20% aqueous sodium carbonate, stirred for 1/2 hour at 10°-20°, and filtered. The filtrate is combined with 250 ml 12% aqueous sodium carbonate, stirred for 1/2 hour, again filtered, both residues are washed with about 3 lt of water, combined and dried, to yield 300 of 6-chloro-3-dimethylaminomethylindole melting at 130°-133°.

Provenance & Evidence