Methyl iodide → HCID 70426537, compound

Participants

Reaction Steps

A solution of methyl iodide (0.83 g) in tetrahydrofuran (50 ml) was added at room temperature to a solution of 3-[2-[(phenylmethyl)amino]ethyl]-1H-indole-5-acetamide (1.8 g) and diisopropylethylamine (0.76 g) in dry tetrahydrofuran (150 ml). The resulting solution was stirred at room temperature for 16 h and was then evaporated in vacuo to dryness. The residue was partitioned between chloroform (225 ml) and 8% aqueous sodium hydrogen carbonate (250 ml). The organic layer was run off and the aqueous layer extracted with more chloroform (200 ml). The combined organic solutions were dried (Na2SO4), filtered and evaporated to afford a gum (1.6 g) which was purified by column chromatography on silica gel (Merck Type 60, 250 g) eluting with methanol in chloroform (1-10%). The product-bearing fractions afforded the title compound as a pale yellow oil which slowly crystallised on standing 0.4 g m.p. 123°-126° (bubbles above 93°).

Provenance & Evidence