4-(Aminomethyl)piperidine → HCID 57180202, compound

N,N-Dimethylformamide dimethyl acetal (23.3 ml) was added to 4-aminomethylpiperidine (20.0 g) in toluene (20 ml) and the mixture was boiled under reflux for 3 hours removing the water formed using a Dean and Stark apparatus to give a solution of 4-(dimethylaminomethyliminomethyl)piperidine. The mixture was cooled to ambient temperature and 2-bromoethyl phenyl ether (22.1 g) then triethylamine (24.3 ml) were added. The mixture was boiled under reflux for 10 hours and then evaporated to dryness. The residue was dissolved in 2M hydrochloric acid (200 ml) and heated on a steam bath for 24 hours. The mixture was cooled to ambient temperature and washed with dichloromethane. The aqueous layer was basified with 6M sodium hydroxide solution and extracted with dichloromethane to give an oil which was distilled at 186°-242° C. at 0.8 mbar. The distillate was dissolved in methanol (50 ml) and treated with concentrated aqueous ammonia solution (20 ml, specific gravity 0.88) and then left at ambient temperature for 18 hours. The solution was concentrated by evaporation and water (200 ml) was added. The mixture was extracted with dichloromethane to give an oil. The oil was dissolved in ether and treated with ethereal hydrogen chloride. A solid was collected by filtration and recrystallised from propan-2-ol/IMS to give 4-aminomethyl-1-(2-phenoxyethyl)piperidine dihydrochloride, m.p. 212°-214° C.

1. temperatureunder reflux for 3 hours
2. customremoving the water
3. customformed

ORD record

ord-e1d99eaee0314af6aed762dbab47cc20

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05760035