1,2,4-Trichlorobenzene → HCID 22143020, compound

HRID 2297149Notes

Reaction equation

HRID 2297149 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1Cl.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:23]([O-:26])([O-])=O.[Cs+].[Cs+].[CH3:29]N(C=O)C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:23](=[O:26])[CH2:29][N:13]1[CH2:14][CH2:15][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12]1

Participants

5

Reactant 4

HCID 131,2,4-TrichlorobenzeneHCID 6228Dimethylformamide2×HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22143020HCID 22143020, compound

Procedure

1 mmol of 2,4-dichlorophenyl chloride in DMF was added drop wise to 1. mmol of tert-butyl piperazinecarboxylate and 1.2 mmol Cs2CO3 in DMF at room temperature for fourteen hours. The reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The solution was extracted three times with ethyl acetate, dried over sodium sulfate, and purified by column chromatography eluting with 50% ethylacetate and 50% hexane to obtain tert-butyl 4-[2-(2,4-dichlorophenyl)-2-oxoethyl]piperazinecarboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water and ethyl acetate
  3. extractionThe solution was extracted three times with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. custompurified by column chromatography
  6. washeluting with 50% ethylacetate and 50% hexane

Sources & evidence

ORD record
ord-b48a7660cbbc488db72969b95407635f
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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