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

HRID 427558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427558
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-45cb8d6171984fb4bb3deb0632cf2017
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313122B1

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