Pyridine → N1-(4-Bromobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamine

HRID 395708Notes

Reaction equation

HRID 395708 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[O:8][C:9]([NH:11][C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:3][CH:2]=1.N1C=CC=CC=1.[Br:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>C(Cl)(Cl)Cl>[Br:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:18][C:13]2[C:12]([NH:11][C:9]([O:8][CH:7]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[O:10])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:37])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 685154-Bromobenzoyl chlorideHCID 86585755N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamine

Product 1

HCID 86585754N1-(4-Bromobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamineYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamine (300 mg, 0.920 mmol) and pyridine (0.74 mL) in chloroform (5 mL) was treated with 4-bromobenzoyl chloride (405 mg, 1.84 mmol). After 20 h, the mixture was concentrated and the residue partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate and the combined organics were washed with 1 N aqueous sodium hydroxide, water, saturated sodium chloride solution. The solution was dried (potassium carbonate), filtered, and concentrated in vacuo. Recrystallization (methanol/chloroform and hexanes) yielded 200 mg (43%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washthe combined organics were washed with 1 N aqueous sodium hydroxide, water, saturated sodium chloride solution
  5. dry with materialThe solution was dried (potassium carbonate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customRecrystallization (methanol/chloroform and hexanes)

Sources & evidence

ORD record
ord-6532fe22e86a455ca561a71ee07c3ab5
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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