Potassium Carbonate → 3-(3-Aminopropyl)-2-thiazolidinone

Temperatur

60 °C

To a solution of 2-thiazolidinone (0.994 g, 9.64 mmol) in acetonitrile (10 ml) were added N-phthalimido-3-bromopropylamine (2.88 g, 10.7 mmol), potassium carbonate (1.64 g, 11.9 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed about 17 hours, solvent was removed in vacuo, and the resulting solid was redissolved in 1 M potassium chloride and dichioromethane (˜25 ml each). The aqueous phase was separated and extracted with 2×25 ml dichloromethane. The combined organic fraction was dried over sodium sulfate, filtered and dried in vacuo. The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield). To a warmed solution of the phthalimido protected amine (1.53 g, 5.27 mmol) in 6:1 isopropanol:water was added sodium borohydride (1.01 g, 26.7 mmol), and the mixture was stirred at 60° C. for 22 hours. Glacial acetic acid (5.4 ml) was added, and the solution was stirred at 80° C. for 2 hours, then the solution was cooled and dried in vacuo. The product was redissolved in 6 N hydrochloric acid, washed with ether (2×30 ml), then dried in vacuo. The product was purified via recrystallization from hot water.

1. temperatureThe mixture was refluxed about 17 hours
2. customsolvent was removed in vacuo
3. dissolutionthe resulting solid was redissolved in 1 M potassium chloride
4. customThe aqueous phase was separated
5. extractionextracted with 2×25 ml dichloromethane
6. dry with materialThe combined organic fraction was dried over sodium sulfate
7. filtrationfiltered
8. customdried in vacuo
9. customThe crude product was recrystallized from acetone/methanol
10. customto give 1.54 g (55% yield)
11. stirringthe solution was stirred at 80° C. for 2 hours
12. temperaturethe solution was cooled
13. customdried in vacuo
14. dissolutionThe product was redissolved in 6 N hydrochloric acid
15. washwashed with ether (2×30 ml)
16. customdried in vacuo
17. customThe product was purified via recrystallization from hot water

ORD-Eintrag

ord-6da9c28a19664bfeac740e7682ca8d60

Quelldatensatz

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06340746B1