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

HRID 20274

Reaction equation

HRID 20274 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[NH:11]1[CH2:21][CH2:20][CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:12]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:21][CH2:20][CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:12]2)=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 4232750Ethyl 1-{[(4-chlorophenyl)amino]thioxomethyl}piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chlorophenyl isothiocyanate (3.5 g, 20.7 mmol), and ethyl isonipecotate (3.19 mL, 20.7 mmol) in dichloromethane (30 mL) was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, the residue was triturated with ether and the resulting solid was filtered off and dried to afford the title compound as a white solid, 6.27 g.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was triturated with ether
  3. filtrationthe resulting solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-73152c6a580141a5a9788acf25312ca4
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

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