Chloroacetaldehyde → 2-(1-(3,5-Dichloropyridin-4-yl)piperidin-4-yl)thiazole

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carbothioamide 24 (23 mg, 0.079 mmol) in ethanol (2 mL) was added chloroacetaldehyde (50% wt in H2O) (0.26 mL, 0.16 mmol) and the mixture was heated at reflux for 17 h. The mixture was concentrated and chloroform (10 mL) was added to the residue. The solution was washed with water (10 mL) and extracted with chloroform (10 mL). The combined organic extracts were washed with brine (10 mL), dried (MgSO4) and concentrated under reduced pressure to furnish a brown oil (40 mg). The crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 10:1, then hexane, EtOAc, 1:1) to furnish the title compound as a pale brown solid (5 mg, 20%), LC-MS (ESI) Rt 2.79 min, m/z 314 (100%, M+).

1. temperaturethe mixture was heated
2. temperatureat reflux for 17 h
3. concentrationThe mixture was concentrated
4. additionchloroform (10 mL) was added to the residue
5. washThe solution was washed with water (10 mL)
6. extractionextracted with chloroform (10 mL)
7. washThe combined organic extracts were washed with brine (10 mL)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated under reduced pressure

ORD record

ord-b081def3bd90435bb67c34bd9a8b5571

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778925B2