3,5-Dichlorophenyl isocyanate → Ethyl 4-[(3,5-dichloroanilino)carbonyl]-2-piperazinecarboxylate

HRID 1976460Notes

Reaction equation

HRID 1976460 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:12][C:13]1[CH:14]=[C:15]([N:20]=[C:21]=[O:22])[CH:16]=[C:17]([Cl:19])[CH:18]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[NH:20][C:21]([N:4]1[CH2:5][CH2:6][NH:1][CH:2]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3]1)=[O:22]

Participants

4

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 10633257Ethyl Piperazine-2-carboxylate

Product 1

HCID 22644956Ethyl 4-[(3,5-dichloroanilino)carbonyl]-2-piperazinecarboxylateYield 27%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 2-piperazinecarboxylate (0.9 g, 5.7 mmol) in chloroform (11 mL) was added 3,5-dichlorophenyl isocyanate (1.05 g, 5.7 mmol). The reaction was stirred overnight after which time a precipitate had formed. The reaction was concentrated and the solid was chromatographed on silica gel using ethyl acetate as eluant to provide 0.53 g (27%) of ethyl 4-[(3,5-dichloroanilino)carbonyl]-2-piperazinecarboxylate as an off white powder. Electrospray Mass Spec 346.1 (M+H)+.

Workup

  1. customhad formed
  2. concentrationThe reaction was concentrated
  3. customthe solid was chromatographed on silica gel

Sources & evidence

ORD record
ord-27c2dc7de1c84ecc93a4319d5aa70bb3
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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