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

HRID 2189263노트

반응식

HRID 2189263 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ae8829c787794d65813b74d708d683af
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324225B2

반응 노트

불러오는 중…