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

HRID 2189263ノート

反応式

HRID 2189263 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ae8829c787794d65813b74d708d683af
出典データセット
uspto-grants-2012_12
特許番号
US08324225B2

反応ノート

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