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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 507372Generated: October 26, 2026

N-methyl-2-pyrrolidone → Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

https://huagongshe.com/reaction/507372

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-methyl-2-pyrrolidoneHCID 13387—
Reactant5-Bromo-N,N-DimethyltryptamineHCID 360252—
ReactantHCID 178418546HCID 178418546—
SolventAmmoniaHCID 222—
ProductIndole-5-carbonitrile, 3-(2-dimethylaminoethyl)-HCID 28511—

Reaction Conditions

Temperature200 °C

Reaction Steps

A flask is charged with 5-bromo-dimethyltryptamin (5.34 g, 20 mmol), copper (I)cyanide (2.69 g, 30 mmol), and N-Methylpyrrolidone (20 ml). The mixture is heated at 200° C. for 9 hours under a nitrogen atmosphere and then left stirring over night. The brown mixture is poured on water to give a brown precipitate. This is suspended in ammonia (100 ml 25% solution in water), and the mixture is stirred over night. Extraction with TBME (3*100 ml), and removal of the solvent from the dried (sodium sulfate) organic layer gives the title product as a yellow solid (properties as in Reference Example 3).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07786156B2
Source datasetuspto-grants-2010_08
ORD IDord-2d93bcf7986a4b8dbdebd94692561d1b
Source noteuspto-grants-2010_08