HCID 67541966, compound → HCID 16006724, compound

Participants

Reaction Conditions

Reaction Steps

To a sealed tube reaction vessel were added cis-6-(4-bromo-phenyl)-9-(3-piperidin-1-yl-propoxy)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline (0.21 mmol), CuCN (5.2 equiv.), and DMF (1.7 M). The tube was purged with nitrogen, sealed, and heated at 150° C. overnight. The reaction mixture was cooled to rt, diluted with aqueous NaCN, and extracted with diethyl ether. The organic layer was washed with water, satd. aq. NaHCO3, and brine, dried (Na2CO3), and concentrated to give the crude product. Chromatographic purification (NH3 in MeOH/CH2Cl2) followed by reverse-phase HPLC gave the desired product as a mixture with the 6-trans isomer (7% combined yield).

Provenance & Evidence