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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 619489Generated: October 30, 2026

Water → HCID 21190120, compound

https://huagongshe.com/reaction/619489

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactanttert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 15512811—
Reactant1,2-Dihydro-3-methyl-1,4,7b-triazacyclopent[cd)inden-2-oneHCID 135810294—
SolventDimethylformamideHCID 6228—
ProductHCID 21190120HCID 2119012062.9%

Reaction Steps

To a suspension of 735 mg (4.24 mmol) of 1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one in 15 ml of DMF was added, while stirring under ice-cooling, 187 mg (4.68 mmol) of 60% sodium hydride (dispersion in oil). The mixture was stirred for 20 minutes at the same temperature. To the mixture was added a solution of 1.18 g (4.24 mmol) of 4-bromomethyl-1-tert-butoxycarbonylpiperidine in 5 ml of DMF. The mixture was stirred for one hour at 100° C. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to give 988 mg of the desired compound (62.8%, pale yellow solid).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05958942
Source datasetuspto-grants-1999_09
ORD IDord-b324e46ba23f414e9c5c7c6ba587b8d3
Source noteuspto-grants-1999_09