3-(4-Piperidinyl)-1H-indole → HCID 10416821, compound

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Reaction Steps

The diastereoisomer mixture of (4-dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid phenyl ester (599 mg, 1.7 mmole) was added to a solution of 3-piperidine-4-yl-1H-indole (340.5 mg, 1.7 mmole) in dioxane (12 ml). The reaction mixture was a clear solution above 40° C., and this solution was boiled for 24 hours under reflux. No precipitate was formed even at RT. The solvent was distilled off in vacuo. The residue contained, besides phenol, the two diastereoisomers of 4-(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 (75 g). Methanol/EE (1:1; 800 ml) and methanol (500 ml) were used as eluent. The non-polar diastereoisomer (281 mg, m.p. 89°-93° C., 36%) and the polar diastereoisomer of 4-(1H-indol-3-yl)piperidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (262 mg, m.p. 104°-107° C., 34%) were thereby obtained in pure form.

Provenance & Evidence