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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 356002Generated: October 27, 2026

Sodium Bicarbonate → 5-methoxy-3-[N-(4-(4-fluoro-phenyl)-4-oxo-butyl)piperidin-3-ylmethyl]-1-H-indole

https://huagongshe.com/reaction/356002

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
Reactant2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 2723778—
Reactant5-methoxy-3-(piperidin-3-ylmethyl)-1H-indoleHCID 18940825—
SolventDimethylformamideHCID 6228—
SolventTetrahydrofuranHCID 8028—
Product5-methoxy-3-[N-(4-(4-fluoro-phenyl)-4-oxo-butyl)piperidin-3-ylmethyl]-1-H-indoleHCID 18940872—

Reaction Steps

A mixture of compound of Description 6 [5-methoxy-3-(piperidin-3-ylmethyl)-1H-indole] (2 g; 0.0082 mol), sodium bicarbonate (0.68 g; 0.0082 mol), KI (0.087 g; 0.00053 mol) and 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [2.2 g (1,8 ml); 0.009 mol] in dry dimethylformamide (25 ml) and tetrahydrofuran (25 ml), was heated under reflux for 5 hours. After evaporation under vacuum, the residue was flash chromatographed on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0.5) and the desired compound was obtained. A solution of the compound in ethanol was saturated with gaseous hydrogen chloride, a solid was precipitated. The title compound hydrochloride was collected by filtration.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05834493
Source datasetuspto-grants-1998_11
ORD IDord-8d8eec3188d9472e9532490aecf20030
Source noteuspto-grants-1998_11