O-Phenylenediamine → 4-[3-(2-Amino-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2047368Notes

Reaction equation

HRID 2047368 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=O)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]1([NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:22])[NH:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH2:30])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 448287263-(4-(Tert-butoxycarbonyl)piperazin-1-yl)benzoic acid

Product 1

HCID 686708464-[3-(2-Amino-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(3-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (5.80 g, 18.95 mmol) and 1,1-carbonyldiimidazole (CDI) (3.07 g, 18.95 mmol) in acetonitrile (120 mL) was stirred for 3 h at room temperature, then 1,2-phenylenediamine (2.25 g, 20.85 mmol) was added. The resulting suspension was refluxed for 3 h, then cooled to room temperature and the solvent removed under reduced pressure. The resulting residue was diluted with dichlomethane (200 mL), washed with water (3×40 mL) and the organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was recrystallized from EtOAc to obtain 2.99 g (40%) of the title compound.

Workup

  1. temperatureThe resulting suspension was refluxed for 3 h
  2. customthe solvent removed under reduced pressure
  3. additionThe resulting residue was diluted with dichlomethane (200 mL)
  4. washwashed with water (3×40 mL)
  5. dry with materialthe organic layer dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product was recrystallized from EtOAc

Sources & evidence

ORD record
ord-0cc6babdcd19429886b0b8e0fd4c39fd
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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