Ammonia → HCID 18797048, compound

Participants

Reaction Steps

A mixture of 7-Bromo-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (3.84 g, 8.3 mmol) and copper (I) cyanide (1.04 g, 11.4 mmol) in N-methyl-2-pyrrolidinone (20 ml) was heated at reflux for 1.5 h. The cooled mixture was poured onto 0.880 ammonia (50 ml) and crushed ice (~50 g) with stirring. The product was extracted into ethyl acetate (100 ml) and washed further with 0.880 ammonia (2×30 ml), then brine. Drying (Na2SO4) and evaporation of the solvent in vacuo afforded a brown oil. Chromatography on silica using 20-100% ethyl acetate-pentane gradient elution afforded the title compound as a colourless gum (1.58 g, 47%).

Provenance & Evidence