Piperidine → HCID 58860794, compound

A mixture of 3-thiophenecarboxaldehyde (1.40 mL, 15.0 mmol), (4-methanesulfonylphenyl)acetic acid (3.23 g, 15.0 mmol), and piperidine (0.45 mL, 4.5 mmol) in PhMe (21 mL) was heated under reflux with stirring for 16 h. On cooling, the PhMe was decanted off from the oily solid that had settled at the bottom of the reaction vessel. This solid was partitioned between 1M HCl (60 mL) and EtOAc (400 mL), then the aqueous phase was extracted further with EtOAc (60 mL). The combined organic layers were washed with H2O (60 mL), before being shaken with saturated aqueous Na2CO3 (100 mL). The resulting emulsion was filtered through Celite. The organic layer was extracted further with saturated aqueous Na2CO3 (2×100 mL). The combined aqueous layers were washed with Et2O (80 mL), before being filtered through Celite and carefully acidified with AcOH to adjust the pH to 4. The off-white precipitate formed was collected, washed thoroughly with H2O, and air dried to furnished the title compound: m/z (ES+)=634.2 [2M+NH4]+.

1. temperaturewas heated
2. temperatureunder reflux
3. temperatureOn cooling
4. customthe PhMe was decanted off from the oily solid that
5. customThis solid was partitioned between 1M HCl (60 mL) and EtOAc (400 mL)
6. extractionthe aqueous phase was extracted further with EtOAc (60 mL)
7. washThe combined organic layers were washed with H2O (60 mL)
8. stirringbefore being shaken with saturated aqueous Na2CO3 (100 mL)
9. filtrationThe resulting emulsion was filtered through Celite
10. extractionThe organic layer was extracted further with saturated aqueous Na2CO3 (2×100 mL)
11. washThe combined aqueous layers were washed with Et2O (80 mL)
12. filtrationbefore being filtered through Celite
13. customThe off-white precipitate formed
14. customwas collected
15. washwashed thoroughly with H2O, and air
16. customdried

ORD record

ord-278333f55c7f4981927f313953e9ce35

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582632B2