2,5-Dichlorobenzoic acid → {2-[4-(2,5-Dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

HRID 1178150Notes

Reaction equation

HRID 1178150 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](=[O:59])[NH:49][CH2:50][C:51](=[O:58])[N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)([CH3:46])([CH3:45])[CH3:44]>CN(C=O)C.O>[C:43]([O:47][C:48](=[O:59])[NH:49][CH2:50][C:51]([N:52]1[CH2:53][CH2:54][N:55]([C:23](=[O:25])[C:22]2[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:21]=2[Cl:20])[CH2:56][CH2:57]1)=[O:58])([CH3:46])([CH3:44])[CH3:45]

Participants

8

Reactant 5

HCID 57842,5-Dichlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17750349tert-butyl N-(2-oxo-2-(piperazin-1-yl)ethyl)carbamate

Product 1

HCID 59559606{2-[4-(2,5-Dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl esterYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (125 mg, 0.93 mmol) and DIPEA (207 mg, 2.2 mmol) were added to a stirred solution of 2,5-dichloro-benzoic acid (141 mg, 0.74 mmol) in DMF (2.5 mL). The mixture was then cooled to 10° C. and EDCI.HCl (178 mg, 0.93 mmol) followed by (2-oxo-2-piperazin-1-yl-ethyl)-carbamic acid tert-butyl ester (200 mg, 0.82 mmol) were added. The reaction mixture was then stirred at room temperature overnight. Water was added, and the product was extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification using column chromatography (silica gel (60-120 mesh) using 30% ethyl acetate in hexane as the eluent) afforded {2-[4-(2,5-dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester as a solid in 91.2% yield. LC-MS purity: 99.48%.

Workup

  1. additionwere added
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-c81ad93bae154f6496ff5b114e0d7546
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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