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

HRID 20276

Reaction equation

HRID 20276 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 (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.

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-0fb11775f62b47738fcab9cbb4c48873
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

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