Cesium carbonate → HCID 22143020, compound

HRID 1823459Notes

Reaction equation

HRID 1823459 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4](=[O:7])[CH2:5]Cl.[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4](=[O:7])[CH2:5][N:16]1[CH2:15][CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 202502,2',4'-TrichloroacetophenoneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22143020HCID 22143020, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1 mmol of 2,4-dichlorophenacyl 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-b3b63f63f7654cd3a40c586d5ff1b05b
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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