Reaction #48554

Reaction equation

4-chlorophenyl isothiocyanate

ethyl 4-methylpiperidine-4-carboxylate

→

title compound

Ethyl 1-{[(4-chlorophenyl)amino]carbonothioyl}-4-methylpiperidine-4-carboxylate

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe mixture was partitioned between dichloromethane and brine
2. 2
   Otherthe layers were separated
3. 3
   DryingThe organic phase was dried over MgSO4
4. 4
   Otherevaporated under reduced pressure
5. 5
   OtherThe crude product was purified by column chromatography on silica gel

Procedure

A mixture of 4-chlorophenyl isothiocyanate (2.36 g, 13.98 mmol), and ethyl 4-methylpiperidine-4-carboxylate (U.S. 2002/0086887, example 532C) (2.17 g, 12.71 mmol) in dichloromethane (50 mL) was stirred at room temperature for 30 minutes. The mixture was partitioned between dichloromethane and brine, and the layers were separated. The organic phase was dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:ethyl acetate (100:0 to 90:10) to provide the title compound as a white solid, 3.46 g.

Source