Sodium Hydroxide → 1-Methyl-4-(1,2,5,6-tetrahydro-3-pyridinyl)-1H-indole

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Reaction Steps

A solution of 12 g of the product of Example 19 in 360 ml of 1 N hydrochloric acid was refluxed for 4 hours and was cooled in an ice bath while adding sodium hydroxide solution until the pH was alkaline. The mixture was extracted with methylene chloride and the organic phase was washed with aqueous sodium chloride solution, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 6-3-1 chloroform-acetone-triethylamine mixture to obtain 6 g of 1-methyl-4-(1,2,5,6-tetrahydropyridin-3-yl)-1H-indole.

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