5-fluoro-3-(piperidin-4-yl)-1H-indole → HCID 11765016, compound

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Reaction Steps

The diastereoisomer mixture of (4-dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid phenyl ester (387.7 mg, 1.1 mmole) was added to a solution of 5-fluoro-3-piperidine-4-yl-1H-indole (240.1 mg, 1.1 mmole) in dioxane (11 ml). The solution was boiled under reflux for 16 hours. The solution was worked up by distilling off the solvent in vacuo. The residue contained, apart from phenol, also the two diastereoisomers of 4-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide. The diastereoisomers were separated and purified by flash chromatography on silica gel (25 g). Methanol/EE (1:1, 900 ml) was used as eluent. The non-polar diastereoisomer (150 mg, m.p. 95°-98° C., 29%) and the polar diastereoisomer of 4-(5-fluoro-1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (120 mg, m.p. 206°-208° C., 23%) were thereby obtained in pure form.

Provenance & Evidence