1H-indole-3-propylamine → 2-{[3-(Indol-3-yl)-propylamino]-methyl}-2,3,8,9-tetrahydro-7H-1,4-dioxino-[2,3-e]indol-8-one

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(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino-[2,3-e]indol-8-one (1.5 g, 4.2 mmole) in DMSO (80 ml) was slowly added through a dropping funnel to 3-(3-aminopropyl)indole (1.1 g, 6.3 mmole) in DMSO (50 ml) and the mixture was heated at 75° C. for 17 hours. Most of DMSO was removed under reduced pressure and the residue was then partitioned between water and dichloromethane/isopropanol (3/1) solution. The separated organic layer was dried over anhydrous sodium sulfate, filtered, concentrated in vacuum and column chromatographed on silica gel using first ethyl acetate/hexane (7/3), then ethyl acetate and finally 5% methanol in ethyl acetate as eluants. The expected product was isolated, treated with 0.25M ethanolic fumaric acid and precipitated with a minimum amount of hexane to give 70 mg of the (S) enantiomer of the title compound as a tan solid fumarate salt, Mass spec (m/e), 377 (M+).

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