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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 335601Erstellt: 25. Oktober 2026

Acetic Acid → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzothiophene-2-carboxamide dihydrochloride

https://huagongshe.com/reaction/335601

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktAcetic AcidHCID 176—
EduktN-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothiophene-2-carboxamide hydrochlorideHCID 68429753—
KatalysatorZincHCID 23994—
LösungsmittelWaterHCID 962—
ProduktN-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzothiophene-2-carboxamide dihydrochlorideHCID 68431067—

Reaktionsschritte

385.0 mg (1.05 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothio-phene-2-carboxamide hydrochloride are suspended in 10 ml of a 1:1 mixture of acetic acid and water. 300.0 mg (4.59 mmol) of zinc are added, and the mixture is then stirred at RT for 1 h. The reaction mixture is filtered through kieselguhr, and the filter cake is washed with methanol. The filtrate is concentrated under reduced pressure and the residue is purified by preparative HPLC. The product fraction is dissolved in 4M HCl in dioxane, concentrated under reduced pressure and recrystallized from acetonitrile. 233 mg (59.5% of theory) of the title compound are obtained.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08884017B2
Quelldatensatzuspto-grants-2014_11
ORD IDord-0dd8b884a894433fb11aba8b453b0e93
Quellennotizuspto-grants-2014_11