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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2356377Generated: October 23, 2026

1-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1) → HCID 178515135, compound

https://huagongshe.com/en/reaction/2356377

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1)HCID 18401284—
ReactantHCID 178527204HCID 178527204—
CatalystTetrabutylammonium BromideHCID 74236—
SolventWaterHCID 962—
ProductHCID 178515135HCID 178515135—

Reaction Conditions

Temperature85 °C

Reaction Steps

To a stirred solution of 2-methylene-3-quinuclidinone hydrochloride (0.5 g, 3.6 mmol) in water (6 ml) triethylamine (1.5 ml), tetra-n-butyl ammonium bromide (120 mg) and 6-mercapto-purine monohydrate (0.62 g) were added and the reaction mixture was allowed to stir at 85° C. for 14 h. The completion of reaction was monitored by tlc. The reaction mixture was quenched with ice-cold water (10 ml), extracted with dichloromethane (2×25 ml), the organic layers were washed with water, brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified (140 mg, 14%) by flash column chromatography on neutral silica gel using 9:1 chloroform:methanol as eluent.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07759361B2
Source datasetuspto-grants-2010_07
ORD IDord-b2f85378e1124c06bba301649717b441
Source noteuspto-grants-2010_07