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
Participants
| Role | Name | HCID | Charge |
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| Reactant | 1-Bromo-3-chloropropane | HCID 8006 | — |
| Reactant | 2-Pyrrolidone | HCID 12025 | — |
| Reactant | 2-Piperidone | HCID 12665 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Reactant | Potassium | HCID 5462222 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Solvent | Benzene | HCID 241 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | 1-(3-Chloropropyl)pyrrolidin-2-one | HCID 11105662 | — |
| Product | HCID 14526712 | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06084097 |
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| Source dataset | uspto-grants-2000_07 |
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| ORD ID | ord-abd65f5403fc46358f71006d4adca722 |
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| Source note | uspto-grants-2000_07 |
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