Methyl iodide → 2-Methyl-2-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ium iodide

Participants

Reaction Steps

2-phenyl-1,2,3,4-tetrahydroisoquinoline (1.01 g,) was dissolved in acetone (10 ml) and methyl iodide (0.794 g,) was added. The clear solution stood at -20° for 48 hr when t.l.c. indicated the presence of unchanged starting material. A further quantity of methyl iodide (0.3 ml) was added and the reaction mixture was heated at reflux for 3 hrs. The solvent was removed in vacuo and the residue triturated with ether. The resulting solid 1,2,3,4-tetrahydro-2-methyl-2-phenylisoquinolinium iodide was filtered off and dried (1 g). m.pt. softens 190°, melts 195° (decomp.)

Provenance & Evidence