Potassium Carbonate → (n',n'-Dimethyl-3-aminopropyl)-2-thiazolidinone

To a solution of 2-thiazolidinone (4.15 g, 40.18 mmol) in acetonitrile (60 ml) were added potassium carbonate (13.3 g 96.2 mmol), N,N-dimethyl-3-aminopropyl chloride hydrochloride (7.63 g, 48.3 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed for 18 hours, solvent removed in vacuo, then redissolved in dichloromethane and 1 M potassium chloride (40 ml each). The aqueous phase was isolated and extracted twice with 30 ml portions of dichloromethane. The combined organic fraction was washed with saturated sodium chloride (˜50 ml), dried over sodium sulfate, filtered, and dried in vacuo. The crude product was purified via silica gel chromatography, using a 10:1 ratio of silica gel A, 200-425 mesh, and eluting with 5% methanol in chloroform, yielding 1.15 g (15%) pure product.

1. temperatureThe mixture was refluxed for 18 hours
2. customsolvent removed in vacuo
3. dissolutionredissolved in dichloromethane
4. customThe aqueous phase was isolated
5. extractionextracted twice with 30 ml portions of dichloromethane
6. washThe combined organic fraction was washed with saturated sodium chloride (˜50 ml)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customdried in vacuo
10. customThe crude product was purified via silica gel chromatography
11. washeluting with 5% methanol in chloroform

ORD record

ord-dcdf44c666934032a468821839cc6fdd

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07425635B2