Benzylamine → HCID 11461445, compound

To a solution of 4-benzylpiperidine (10.0 g, 57 mmol) and DBU (85 μl, 0.57 mmol) in THF (10 ml) was dropwise added a solution of acrolein (90%, 3.2 g, 57 mmol) in THF (2 ml) at −20° C. with stirring over a period of 10 minutes. The mixture was stirred for 1 hour while the temperature of the mixture was elevating from −20° C. to −10° C. To the mixture were added benzylamine (6.1 g, 57 mmol), sodium triacetoxyborohydride (24.2 g, 114 mmol), successively, at −10° C., and the mixture was stirred 19 hours while the temperature was elevated to room temperature. To the mixture was added aqueous solution of 2N-sodium hydroxide (100 ml) under ice cooling, and the mixture was stirred for 30 minutes and extracted with diethyl ether (100 ml, 80 ml×2). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was dissolved in 2-propanol (50 ml). To the solution was added 4N-hydrogen chloride in ethyl acetate (50 ml) with stirring, and the resulting precipitates were collected by filtration. The precipitates were washed with 2-propanol (20 ml×3), and dried under reduced pressure to give the titled compound as white crystals (6.5 g). To the white crystaline (2.0 g) obtained was added aqueous solution of 1N-sodium hydroxide (10 ml), and the resulting solution was extracted by ethyl acetate (10 ml, 8 ml×2). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give the titled compound (1.6 g) as a colorless oily substance.

1. stirringThe mixture was stirred for 1 hour while the temperature of the mixture
2. customwas elevating from −20° C. to −10° C
3. stirringsuccessively, at −10° C., and the mixture was stirred 19 hours while the temperature
4. customwas elevated to room temperature
5. stirringthe mixture was stirred for 30 minutes
6. extractionextracted with diethyl ether (100 ml, 80 ml×2)
7. dry with materialThe organic layer was dried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. dissolutionThe concentrate was dissolved in 2-propanol (50 ml)
10. additionTo the solution was added 4N-hydrogen chloride in ethyl acetate (50 ml)
11. stirringwith stirring
12. customthe resulting precipitates
13. filtrationwere collected by filtration
14. washThe precipitates were washed with 2-propanol (20 ml×3)
15. customdried under reduced pressure

ORD record

ord-a59600321fde425bb02139e3494e7af0

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562978B1