3-Aminobenzoic Acid → 3-((4-Methyl-1-piperazinyl)carbonyl)aniline

HRID 2189263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189263
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]([C:5]([N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)=[O:7])[CH:8]=[CH:9][CH:10]=1

Komponenten

7

Edukt 5

HCID 74193-Aminobenzoic AcidHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 167732183-((4-Methyl-1-piperazinyl)carbonyl)anilineAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-aminobenzoic acid (1.51 g, 11 mmol), 1-methylpiperazine (1.1 mL, 10 mmol), EDCI.HCl (2.87 g, 15 mmol) and Et3N (2.8 mL, 20 mmol) in CH2Cl2 (10 mL) is stirred at room temperature for 20 hours. Then saturated NaHCO3 aqueous solution is added. The aqueous layer was extracted with CH2Cl2, and the organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93) to give 1.75 g of the title compound as a yellow solid.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. dry with materialthe organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93)

Quellen und Nachweise

ORD-Eintrag
ord-ae8829c787794d65813b74d708d683af
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324225B2

Notizen zur Reaktion

Wird geladen…