Sodium Iodide → HCID 86737805, compound

Participants

Reaction Steps

3-(1-Imidazolylmethyl)indole (3.94 g) was dissolved in N,N-dimethylformamide (50 ml) and the solution was treated with sodium hydride (1.00 g of 50% dispersion in oil) as described in Example 44. To the solution of the anion at 0° C. was added sodium iodide (3.0 g) and N-(3-bromopropyl)phthalimide (5.36 g) over 10 minutes. The mixture was then stirred at room temperature for 20 hours and evaporated to dryness. The residue was chromatographed on silica gel. The column was first eluted with petrol (b.p. 40°-60° C.) to remove mineral oil and then with chloroform to remove the product. The chloroform eluate was evaporated to give a viscous gum which was pure enough for further reaction. A portion was dissolved in ethyl acetate and the solution was treated with an excess of fumaric acid in ethyl acetate. The solid was filtered off and crystallised from ethyl acetate containing a trace of ethanol to give 1-(3-phthalimidopropyl)-3-(1-imidazolylmethyl)indole fumarate, m.p. 166°-167° C. Found: C, 64.56; H, 4.78; N, 11.09. C23H20N4O2.C4H4O4 requires: C, 64.79; H, 4.83; N, 11.20.

Provenance & Evidence