3-Chloro-1-propanol → 1-(2-Chloroethyl)pyrrolidine hydrochloride

165 ml (2 mol) of tetrahydropyrrole, 67 ml (1 mol) of 3-chloropropanol and 200 ml toluene were added successively into a reaction flask. The mixture was heated to the reflux temperature and reacted for 3 h. After cooling to room temperature, a solid was separated out. The solid was filtered by sucking, and the filter cake was washed with 20 ml toluene. The temperature of the filtrate was controlled at about 75° C., and 200 ml thionyl chloride was added dropwise. After refluxing for 2 h, the mixture was cooled to room temperature and then concentrated to dry in a reduce pressure. The residue was recrystallized with absolute ethyl alcohol to obtain 105 g white solid with the yield of 62.3%. m.p. 169-173° C.

1. temperatureThe mixture was heated to the reflux temperature
2. customreacted for 3 h
3. customa solid was separated out
4. filtrationThe solid was filtered
5. washthe filter cake was washed with 20 ml toluene
6. customwas controlled at about 75° C.
7. addition200 ml thionyl chloride was added dropwise
8. temperatureAfter refluxing for 2 h
9. temperaturethe mixture was cooled to room temperature
10. concentrationconcentrated
11. customto dry in a reduce pressure
12. customThe residue was recrystallized with absolute ethyl alcohol

ORD record

ord-11dfc5714ca8442fa9fa050e12ea5fa3

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664238B2