Diphosgene → HCID 18783806, compound

HRID 1108666Notes

Reaction equation

HRID 1108666 reaction equation
FC(F)(F)C([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=O.ClC([O:24][C:25](Cl)=[O:26])(Cl)Cl.[O:28]1[CH2:33]COCC1>>[N:8]1([C:11]2[CH:12]=[CH:13][C:14]([NH:15][C:33]([N:5]3[CH2:10][CH2:9][N:8]([CH2:11][C:25]([OH:24])=[O:26])[CH2:7][CH2:6]3)=[O:28])=[CH:16][CH:17]=2)[CH2:7][CH2:6][NH:5][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 10426DiphosgeneHCID 312751,4-DioxaneHCID 17047043HCID 17047043, compound

Product 1

HCID 18783806HCID 18783806, compoundYield 37%

Procedure

4-[4-(trifluoroacetyl)-1-piperazinyl]aniline 4 (250 mg, 0.9 mmole) was dissolved in dioxane (5 ml) and TEA (125(1, 0.9 mmole). Trichloromethylchloroformate (110(1, 0.9 mmole) was added dropwise via syringe. Solid precipitated out upon addition, mixture stirred 30 min and was filtered to yield the title compound as a white solid (10 mg, 37%). MS (ES) m/e 300.2 [M+H]+

Workup

  1. customSolid precipitated out upon addition, mixture
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-32dce5f0231545b393bb4f24c2726014
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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