Piperidine → N-(3-chloropropyl)piperidine hydrochloride

1.72 g (20.3 mmol) of piperidine, 2 ml (24.3 mmol) of 3-chloropropanol and 10 ml toluene were added successively into a reaction flask. The mixture was heated to the reflux temperature and reacted for 4 h. Into the reaction mixture, 5% NaOH 4 ml was added, and the mixture was refluxed for 1 h. After cooling to room temperature, the mixture was washed with 5% NaOH solution. The organic layer was washed with a saturated saline solution, then dried over anhydrous sodium sulfate and filtrated. 3 ml (40.6 mmol) thionyl chloride was added dropwise into the filtrate in an ice-bath, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated to dry in a reduced pressure, and the residue was recrystallized with absolute ethyl alcohol to obtain 2.4 g of a khaki solid with the yield of 59%. m.p. 218-220° C.

1. temperatureThe mixture was heated to the reflux temperature
2. customreacted for 4 h
3. temperaturethe mixture was refluxed for 1 h
4. washthe mixture was washed with 5% NaOH solution
5. washThe organic layer was washed with a saturated saline solution
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltrated
8. concentrationThe reaction solution was concentrated
9. customto dry in a reduced pressure
10. customthe residue was recrystallized with absolute ethyl alcohol

ORD record

ord-5284596c2f5d412a87a6119a0a34e6eb

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664238B2