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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1923403Generated: October 31, 2026

Diethyl Ether → Quinuclidin-4-ylmethanamine

https://huagongshe.com/reaction/1923403

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantSodium HydroxideHCID 14798—
Reactant1-Azabicyclo[2.2.2]octane-4-carbonitrileHCID 141292—
ReactantAluminium lithium hydrideHCID 21226445—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductQuinuclidin-4-ylmethanamineHCID 2205666994%

Reaction Steps

4- Cyanoquinuclidine (0.31 g, 0.0028 moles) was reduced with lithium aluminium hydride (0.45 g, 0.012 moles) in tetrahydrofuran (20 ml) at ambient temperature for 18 hours. Diethyl ether (20 mls) was added followed by water (1.8 ml) and 10%w/v aqueous sodium hydroxide (0.68 ml) and the mixture stirred for 30 minutes. The mixture was then filtered and the filtrate concentrated in vacuo to give the title compound 0.3 g (94%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUSRE043390E1
Source datasetuspto-grants-2012_05
ORD IDord-bbaeeaf588c64c02960459fd74f88c51
Source noteuspto-grants-2012_05