Pentane → 3-(Phenyl(4-(trifluoromethyl)phenyl)methylene)piperidine

To a solution of phenyl(4-(trifluoromethyl)phenyl)methanone (1.5 g, 6.0 mmol) and tert-butyl 3-oxopiperidine-1-carboxylate (1.3 g, 6.5 mmol) in THF (20 mL) was added Zn (1.8 g, 28.5 mmol) and the resulting mixture was stirred at rt for 10 min and was then cooled to 0° C. To this was added TiCl4 (1.4 mL, 13.5 mmol) dropwise. The reaction mixture was stirred first at rt for 15 min and then at 50° C. for 4 h. The solvent was removed under vacuum. Then it was cooled to 0-5° C. and added 2N HCl solution and extracted with ethyl acetate. The combined organic layer was washed with K2CO3 solution, dried over anhydrous sodium sulfate and concentrated under vacuum to afford the crude product. It was cooled to 0-5° C., pentane was added and stirred for 30 min and dried under vacuum to afford 3-(phenyl(4-(trifluoromethyl)phenyl)methylene)piperidine (1.1 g, 57% yield) as a grey solid. MS (ESI, pos. ion) m/z: 318 (M+1).

1. temperaturewas then cooled to 0° C
2. stirringThe reaction mixture was stirred first at rt for 15 min
3. waitat 50° C. for 4 h
4. customThe solvent was removed under vacuum
5. temperatureThen it was cooled to 0-5° C.
6. additionadded 2N HCl solution
7. extractionextracted with ethyl acetate
8. washThe combined organic layer was washed with K2CO3 solution
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under vacuum
11. customto afford the crude product
12. temperatureIt was cooled to 0-5° C.
13. stirringstirred for 30 min
14. customdried under vacuum

ORD 기록

ord-5ac110a6a4754f578f9cad04aea3f559

출처 데이터셋

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08258306B2