Butyl bromide → HCID 19863375, compound

To 10.1 g (0.1 mol) of 2-pyrrolidinemethanol and 13.8 g (0.1 mol) of potassium carbonate in 200 mL of acetonitrile add 13.7 g (0.1 mol) of butyl bromide. Heat the reaction mixture at reflux with stirring under a nitrogen atmosphere. Follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction remove the solvent in vacuo then dissolve the residue in water. Make the aqueous mixture acidic (pH=1) with concentrated hydrochloric acid. Extract the aqueous acid solution with 3×50 mL of hexanes. Make the aqueous solution basic (pH=12) with 20% sodium hydroxide solution and extract with 3×100 mL of methylene chloride. Dry the combined methylene chloride extracts over anhydrous sodium sulfate. Filter the drying agent and evaporate the filtrate in vacuo to obtain the title compound.

1. temperatureHeat the reaction mixture
2. temperatureat reflux
3. customthe progress of the reaction by thin-layer chromatography on silica gel
4. customAt the completion of the reaction remove the solvent in vacuo
5. dissolutionthen dissolve the residue in water
6. extractionExtract the aqueous acid solution with 3×50 mL of hexanes
7. extractionextract with 3×100 mL of methylene chloride
8. dry with materialDry the combined methylene chloride
9. filtrationFilter the drying agent
10. customevaporate the filtrate in vacuo

ORD record

ord-3a4e319aa3b0426db5e270e419fece26

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04906634