Iodide Ion → Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

Participants

Reaction Conditions

Reaction Steps

A flask with mechanical stirrer is charged with 5-iodo-dimethyltryptamine (179 g of 75% purity, 0.427 mol), copper (I)cyanide (90 g, 1.0 mol), and N-methylpyrrolidone (1.5 l). The pink suspension is heated at 180° C. under a nitrogen atmosphere and vigorously stirred, until the iodide is completely consumed (7 h). After cooling to ambient temperature ammonia (2 l 25% solution in water) is added, and the resulting mixture is stirred over night. The mixture is then extracted with TBME (6*1.5 l), and the combined organic layers are washed with water (3*3 l), and brine (1*3 l), and dried (sodium sulfate). Removal of the solvent leaves 75 g (82%) of the product which is >95% pure by HPLC (other properties cf. Reference Example 3).

Provenance & Evidence