Trifluoroacetic acid → 4-(4-Phenoxyphenyl)piperidine

1-Benzyl-4-(4-phenoxy-phenyl)-piperidin-4-ol (3.47 g, 9.6 mmol, prepared in accordance with Example 7) was combined with trifluoroacetic acid (6 mL). The resulting mixture was irradiated at 130° C. in a mono-mode microwave oven for 15 min. The mixture was then concentrated under vacuum, and the obtained residue was triturated with diethyl ether (20 mL). After the solvent was removed under vacuum, the isolated product (6.6 g) was dissolved in methanol (350 mL). To this mixture was added 10% Pd/C was added (800 mg). The resulting suspension was reacted under H2 pressure (4 bar) for 5 hr at 75° C. After removing the catalyst by filtration, the filtrate was concentrated under vacuum. The obtained residue was triturated with diethyl ether (50 mL), and the precipitate was filtered and dried under vacuum. The desired product was obtained as a light yellow solid (3.26 g, 92% yield).

1. customThe resulting mixture was irradiated at 130° C. in a mono-mode microwave oven for 15 min
2. concentrationThe mixture was then concentrated under vacuum
3. customthe obtained residue was triturated with diethyl ether (20 mL)
4. customAfter the solvent was removed under vacuum
5. dissolutionthe isolated product (6.6 g) was dissolved in methanol (350 mL)
6. additionTo this mixture was added 10% Pd/C
7. additionwas added (800 mg)
8. customThe resulting suspension was reacted under H2 pressure (4 bar) for 5 hr at 75° C
9. customAfter removing the catalyst
10. filtrationby filtration
11. concentrationthe filtrate was concentrated under vacuum
12. customThe obtained residue was triturated with diethyl ether (50 mL)
13. filtrationthe precipitate was filtered
14. customdried under vacuum

ORD record

ord-4143a10a49bc4b7ca6f44e73cba79db2

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569495B2