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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1071919Generated: November 3, 2026

Toluene → 1-(prop-2-yn-1-yl)azepane

https://huagongshe.com/reaction/1071919

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantHexamethylenetetramineHCID 4101—
ReactantPropargyl bromideHCID 7842—
ReactantPotassium CarbonateHCID 11430—
SolventAcetonitrileHCID 6342—
Product1-(prop-2-yn-1-yl)azepaneHCID 12688821—

Reaction Conditions

Temperature80 °C

Reaction Steps

18.8 ml of a 3-bromopropyne solution at 80% in toluene are added dropwise to 20.8 ml of hexamethyleneamine and 27.9 g of potassium carbonate in 300 ml of acetonitrile. The reaction mixture is heated at 50° C. for 12 hours and 6 hours at 80° C. The reaction mixture is filtered, and the solvents are evaporated off under reduced pressure. Compound 4.1 is purified by distillation; b.p.=61° C. under a pressure of 26.7 Pa.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06908914B1
Source datasetuspto-grants-2005_06
ORD IDord-e013459f09fb496199697ca6d3c7d7ce
Source noteuspto-grants-2005_06