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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1465992Generated: October 25, 2026

Hydrochloric Acid → 2-(3-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride

https://huagongshe.com/reaction/1465992

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantCarbonate IonHCID 19660—
Reactant6-Bromobenzo[b]thiophen-2-amineHCID 17979823—
ReactantPentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochlorideHCID 86610796—
SolventDimethylformamideHCID 6228—
SolventAcetonitrileHCID 6342—
Product2-(3-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochlorideHCID 86705776—

Reaction Steps

89.2 mg (0.24 mmol) of pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride are dissolved in 1 ml of DMF, mixed with 71.2 mg (0.31 mmol) of 6-bromo-1-benzothiophene-2-amine and stirred at room temperature overnight. 1 g of MP-carbonate (polymer-bound carbonate, capacity: 2.5-3.5 mmol/g; from Argonaut Technologies, USA) is added. After 3 h, the polystyrene resin is filtered off and washed with THF. The combined filtrates are concentrated in vacuo, and the crude product is purified by preparative HPLC. The hydrochloride is prepared by mixing the product with a mixture of 1 M hydrochloric acid and acetonitrile and again concentrating. Drying under high vacuum results in 14 mg (14% of theory) of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09000008B2
Source datasetuspto-grants-2015_04
ORD IDord-25b5c426f6b44148a887d9d05fd69497
Source noteuspto-grants-2015_04