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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1173834Generated: November 2, 2026

Sodium Iodide → 3-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

https://huagongshe.com/reaction/1173834

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium IodideHCID 5238—
ReactantCesium carbonateHCID 10796—
Reactant3-(3-Chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-oneHCID 11710306—
Reactant(3-Bromo-propyl)-dimethyl-amine hydrochlorideHCID 12440776—
Product3-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride saltHCID 11712810—

Reaction Steps

Using the procedure to synthesize Example 12 and using reagents 3-(3-chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (150 mg, 0.412 mmol), (3-bromo-propyl)-dimethyl-amine hydrochloride (167 mg, 0.824 mmol), sodium iodide (62 mg, 0.412 mmol), and cesium carbonate (1.07 g, 3.30 mmol) afford the freebase of the title compound. Dissolve freebase in dichloromethane (5 mL) and add HCl in ether (2M, 0.4 mL), concentrate to give title compound (105 mg, 52%) as a yellow solid: Mass spectrum (apci) m/z=449.3 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07834194B2
Source datasetuspto-grants-2010_11
ORD IDord-6dd880a8ec774983a6223b7864b974f6
Source noteuspto-grants-2010_11