Methyl iodide → HCID 19710005, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(7-methoxy-2-benzofuranyl)pyridine (66 g), methyl iodide (56.7 g) and 2-butanone (800 ml) was stirred at 50° C. for 4 hours, cooled to room temperature, filtered and the resulting solid was washed with 2-butanone to provide 1-methyl-4-(7-methoxy-2-benzofuranyl)pyridinium iodide, m.p. 225°-227° (dec.). The quaternary salt (90 g) was dissolved in methanol (1 l) and a solution of NaBH4 (40 g) in H2O (250 ml) was added dropwise. The mixture was stirred at ambient temperature for 3 hours, concentrated and the residual aqueous layer was extracted with DCM. The extracts were combined, washed with brine and concentrated to give 1-methyl-4-(7-methoxy-2-benzofuranyl)-1,2,3,6-tetrahydropyridine.

Provenance & Evidence