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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2287633Generated: October 30, 2026

1-Bromo-3-chloropropane → 1-(3-Chloropropyl)pyrrolidin-2-one

https://huagongshe.com/reaction/2287633

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Bromo-3-chloropropaneHCID 8006—
Reactant2-PyrrolidoneHCID 12025—
Reactant2-PiperidoneHCID 12665—
ReactantSodiumHCID 5360545—
ReactantPotassiumHCID 5462222—
ReactantPotassium tert-butoxideHCID 23665647—
SolventBenzeneHCID 241—
SolventTolueneHCID 1140—
SolventO-XyleneHCID 7237—
Product1-(3-Chloropropyl)pyrrolidin-2-oneHCID 11105662—
ProductHCID 14526712HCID 14526712—

Reaction Steps

In the first method the 2-pyrrolidone (2, n=1) or 2-piperidone (2, n=2) is condensed with 1-bromo-3-chloropropane in the presence of bases selected from potassium tert. butoxide, pulverized alkali metals selected from sodium or potassium in nonpolar solvents selected from benzene, xylene, toluene at a temperature ranging from 110 to 150° C. for 1.15 to 14 hrs to give 1-chloro-3-[2-oxo-pyrrolidin-1-yl]propane (3, n=1) or 1-chloro-3-[2-oxopiperidin-1-yl]propane (3, n=2) which on condensation with appropriately substituted piperazines, gave the required compounds of formula 1. This reaction may be carried out in solvents selected from acetone, methylethyl ketone, tetrahydrofuran or dimethylformamide using bases selected from triethylamine, pyridine, sodium or potassium carbonate and catalysts selected from sodium/potassium iodide to improve the yield of the compound of formula 1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06084097
Source datasetuspto-grants-2000_07
ORD IDord-abd65f5403fc46358f71006d4adca722
Source noteuspto-grants-2000_07