Diisopropylethylamine → 1-(4,6-Dimethylpyridin-3-yl)-4-(toluene-4-sulfonyl)piperazine

HRID 2411226

反応式

HRID 2411226 の反応式
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.Cl[CH2:20][CH2:21][N:22]([CH2:33][CH2:34]Cl)[S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>O>[CH3:9][C:3]1[CH:4]=[C:5]([CH3:8])[N:6]=[CH:7][C:2]=1[N:1]1[CH2:34][CH2:33][N:22]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH2:21][CH2:20]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 70606694,6-Dimethylpyridin-3-amine

生成物 1

HCID 712521811-(4,6-Dimethylpyridin-3-yl)-4-(toluene-4-sulfonyl)piperazine収率 15.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 5-amino-2,4-dimethylpyridine (883 mg) were added N,N-diisopropylethylamine (2.1 mL) and N,N-bis(2-chloroethyl)-p-toluenesulfonamide (2.08 g), and the mixture was stirred with heating under reflux. After completion of the reaction, water was added to the reaction mixture, the mixture was extracted with chloroform, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give 1-(4,6-dimethylpyridin-3-yl)-4-(toluene-4-sulfonyl)piperazine (380 mg). The obtained 1-(4,6-dimethylpyridin-3-yl)-4-(toluene-4-sulfonyl)piperazine (380 mg) was dissolved in acetic acid (2 mL), 40% hydrobromic acid (2 mL) was added, and the mixture was stirred at 100° C. After completion of the reaction, the reaction mixture was neutralized with aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer to give the title compound (131 mg).

後処理

  1. temperaturewith heating
  2. temperatureunder reflux
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with chloroform
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by column chromatography (chloroform:methanol)

出典と根拠

ORDレコード
ord-eb0674f3edd244f3995b85e2b604a5a1
出典データセット
uspto-grants-2014_08
特許番号
US08816079B2

関連ノート

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