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

HRID 427558Notes

Reaction equation

HRID 427558 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]([NH:17][C:18]3[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:16])[CH2:9][CH2:8]2)=[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:24][C:19]2[C:18]([NH:17][C:15]([O:14][CH2:13][CH:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:12][CH2:11]3)=[O:16])=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:37])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 685154-Bromobenzoyl chlorideHCID 10829995N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamine

Product 1

HCID 21352715N1-(4-Bromobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl)-1,2-benzenediamineYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N1-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl)-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-45cb8d6171984fb4bb3deb0632cf2017
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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