1-Piperidinecarboxaldehyde → HCID 59593369, compound

Temperature

78 °C

(5-Bromo-6-methyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-amine (34, 1.7 g, 4.93 mmol) was dissolved in tetrahydrofuran (40 mL) and cooled at 78° C. under a nitrogen atmosphere. To this mixture was added methyllithium (1.6 M in diethyl ether, 5.91 mmol) dropwise over 20 minutes. After the addition of methyllithium was completed, the reaction mixture was stirred at −78° C. for 2 hours. To this mixture was added tert-butyllithium (1.7 M in pentane, 10.85 mmol) and the mixture was stirred for 4 hours. The reaction mixture was maintained at −78° C., and 1-piperidinecarboxaldehyde (0.60 mL, 5.42 mmol) was added dropwise. The reaction was allowed to stir at −78° C. for an additional 2 hours and warming to 25° C. was achieved from the slow evaporation of the dry ice/acetone cooling bath. The reaction was quenched with ice cold saturated sodium chloride and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. Concentration under reduced pressure afforded an orange oil (35, 1.4 g, 4.93 mmol).

1. stirringthe mixture was stirred for 4 hours
2. temperatureThe reaction mixture was maintained at −78° C.
3. stirringto stir at −78° C. for an additional 2 hours
4. temperaturewarming to 25° C.
5. customwas achieved from the slow evaporation of the dry ice/acetone cooling bath
6. customThe reaction was quenched with ice cold saturated sodium chloride
7. extractionthe resulting mixture was extracted with ethyl acetate
8. dry with materialThe organic layer was dried over magnesium sulfate
9. filtrationfiltered
10. concentrationConcentration under reduced pressure
11. customafforded an orange oil (35, 1.4 g, 4.93 mmol)

ORD record

ord-0d2de3fa9981411d9fc8ac0f65a84b8a

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169250B2