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

HRID 2189263Notes

Reaction equation

HRID 2189263 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 167732183-((4-Methyl-1-piperazinyl)carbonyl)anilineYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ae8829c787794d65813b74d708d683af
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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