2,5-Dichlorobenzoic acid → HCID 17480368, compound

HRID 1665580Notes

Reaction equation

HRID 1665580 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:20][C:21]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]>CN(C=O)C.O>[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:23](=[O:25])[C:22]2[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:21]=2[Cl:20])[CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:44])[CH3:45]

Participants

8

Reactant 5

HCID 57842,5-Dichlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 17480368HCID 17480368, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (213 mg, 1.5 mmol) and DIEA (508 mg, 3.9 mmol) were added to a stirred solution of 2,5-dichlorobenzoicacid (250 mg, 1.3 mmol) in DMF (2.5 mL). The reaction mixture was then cooled to 10° C. and EDCI.HCl (302 mg, 1.5 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (260 mg, 1.3 mmol) were added. The resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with water and the product extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure to afford the crude residue which was purified by column chromatography using silica gel 60-120 mesh (30% ethyl acetate in hexane) to afford 396 mg (84%) of 4-(2,5-dichloro-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester, LCMS: 360.08 (M+1)+, 98.2%.

Workup

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cf8b630f789f4f77b68e3c4fb2fce8ce
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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