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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1987757Generated: October 27, 2026

Sodium Bicarbonate → 4-(+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-1-(4-imidazol-1-ylphenyl)piperazine

https://huagongshe.com/reaction/1987757

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant1-(4-(1H-imidazol-1-yl)phenyl)piperazineHCID 23118290—
Reactant2,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-aldehydeHCID 86607354—
CatalystAcetic AcidHCID 176—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Product4-(+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-1-(4-imidazol-1-ylphenyl)piperazineHCID 86608804100.7%

Reaction Steps

0.7 g of 1-(4-imidazol-1-ylphenyl)-piperazine and 0.7 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-aldehyde were dissolved in 20 ml of methylene chloride and 1 ml of acetic acid as a catalyst was added, followed by stirring at room temperature for 30 minutes. To the resulting reaction solution, 1.2 g of sodium triacetoxyborohydride was added, followed by stirring at room temperature for 30 minutes. After the completion of the reaction, the reaction solution was poured into water, neutralized with an aqueous saturated sodium hydrogen carbonate solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, 1.3 g of the objective product was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07553837B2
Source datasetuspto-grants-2009_06
ORD IDord-01284d3bf21943e8ab4e9fc58f50db17
Source noteuspto-grants-2009_06