Benzaldehyde → 4-Aminomethyl-1-N-Cbz-piperidine

Temperature

0 °C

22.2 g(0.2 mol) of 4-aminomethylpiperidine was dissolved in 250 ml of toluene and 21.2 g(0.2 mol) of benzaldehyde was added thereto. The reaction mixture was refluxed for 3 hours with Dean-stack to remove water, and then cooled down to 0° C. 34.2 g(0.2 mol) of benzylchloroformate was added slowly thereto while stirring. The mixture was stirred at room temperature for 3 hours and 220 ml of 1N aqueous KHSO4 solution was added thereto. The mixture was extracted three times with 200 ml of diethylether, and the aqueous layer was basified with 1N aqueous sodium hydroxide solution. The aqueous solution was saturated with sodium chloride. The aqueous layer was extracted three times with 100 ml of dichloromethane, dried over anhydrous magnesium sulfate and distilled under reduced pressure to give 38 g(Yield 91%, Molecular weight 248) of the title compound.

1. temperatureThe reaction mixture was refluxed for 3 hours with Dean-stack
2. customto remove water
3. stirringThe mixture was stirred at room temperature for 3 hours
4. extractionThe mixture was extracted three times with 200 ml of diethylether
5. extractionThe aqueous layer was extracted three times with 100 ml of dichloromethane
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationdistilled under reduced pressure

ORD record

ord-4f531819aea5484797e05990c24a848e

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268363B1