Dimethyl Sulfoxide → N-(3-Chloropropyl)dibutylamine

A mixture of 9.5 g of 3-chloropropanol, 37 ml of dibutylamine and 50 ml of dimethylsulfoxide was stirred at 70°-80° C. for 8 hours. After cooling, water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed from the mixture under reduced pressure. The residue was dissolved in 50 ml of chloroform, and under ice-cooling, 8 ml of thionyl chloride was added dropwise to the solution. After stirring at 50° C. for 3 hours, the solvent was removed from the reaction mixture under reduced pressure. Water was added to the residue and the mixture was washed with diethyl ether. The mixture was made alkaline with potassium carbonate and extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed from the extract under reduced pressure. The residue was purified by silica gel column chromatography (solvent; chloroform:ethanol=20:1) to give 12 g of N,N-dibutyl-3-chloropropylamine (yield: 58%, oily product).

1. temperatureAfter cooling
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed
4. customdried
5. customthe solvent was removed from the mixture under reduced pressure
6. dissolutionThe residue was dissolved in 50 ml of chloroform
7. temperatureunder ice-cooling
8. addition8 ml of thionyl chloride was added dropwise to the solution
9. stirringAfter stirring at 50° C. for 3 hours
10. customthe solvent was removed from the reaction mixture under reduced pressure
11. additionWater was added to the residue
12. washthe mixture was washed with diethyl ether
13. extractionextracted with ethyl acetate
14. washThe extract was washed
15. customdried
16. customthe solvent was removed from the
17. extractionextract under reduced pressure
18. customThe residue was purified by silica gel column chromatography (solvent; chloroform:ethanol=20:1)

ORD record

ord-c296ef2cb6a64f1cbd2008f4b8e7d02c

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05849732