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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 910442Generated: October 29, 2026

Triethylamine → [(3RS,4SR)-1-Benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amine

https://huagongshe.com/reaction/910442

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant4-(Bromomethyl)-2-fluoro-1-(trifluoromethyl)benzeneHCID 2737574—
Reactant[(3RS,4SR)-1-Benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-methyl-amineHCID 67399567—
SolventTetrahydrofuranHCID 8028—
Product[(3RS,4SR)-1-Benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amineHCID 6721844257.4%

Reaction Conditions

Temperature40 °C

Reaction Steps

To a stirred solution of [(3RS,4SR)-1-benzyl-4-(3-chloro-phenyl)-pyrrolidin-3-yl]-methyl-amine (2.20 g, 7.31 mmol) in THF (70 ml) was added 4-bromomethyl-2-fluoro-1-trifluoromethyl-benzene (2.25 g, 8.75 mmol) and Et3N (1.21 ml, 8.75 mmol). The reaction mixture was stirred overnight at 40° C., concentrated under vacuo, diluted with EtOAc, washed with H2O. The organic phase was dried over Na2SO4 and the product purified by flash chromatography (SiO2, EtOAc/Heptane 1:3) to afford 2.0 g (57%) of the title compound as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08022099B2
Source datasetuspto-grants-2011_09
ORD IDord-bb01653f4db84a0486fc5f7ac001d8f9
Source noteuspto-grants-2011_09