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

HRID 419847

Reaction equation

HRID 419847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[CH3:11][C:12]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:15]2[CH2:16][CH2:17][C:12]([CH3:11])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:14]2)=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 19361805Ethyl 4-methylpiperidine-4-carboxylate

Product 1

HCID 59619551Ethyl 1-{[(4-chlorophenyl)amino]carbonothioyl}-4-methylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chlorophenyl isothiocyanate (2.36 g, 13.98 mmol), and ethyl 4-methylpiperidine-4-carboxylate (US 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.

Workup

  1. customThe mixture was partitioned between dichloromethane and brine
  2. customthe layers were separated
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-100e3de3906944d8b99bc62cc611ba76
Source dataset
uspto-grants-2012_01
Patent number
US08093400B2

Linked notes

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