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Sodium Hydroxide → 1H-Benzimidazole, 2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1-(2-(2-propynyloxy)ethyl)-, (E)-2-butenedioate (1:2)

HRID 1388160
ノート
印刷プレビュー

反応式

HRID 1388160 の反応式
Cl[C:2]1[N:6]([CH2:7][CH2:8][O:9][CH2:10][C:11]#[CH:12])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=1.[CH3:17][N:18]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[OH-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[CH2:10]([O:9][CH2:8][CH2:7][N:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=[C:2]1[N:21]1[CH2:22][CH2:23][CH2:24][N:18]([CH3:17])[CH2:19][CH2:20]1)[C:11]#[CH:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 2283491-MethylhomopiperazineHCID 444972Fumaric AcidHCID 15585274HCID 15585274、化合物

生成物 1

HCID 64484211H-Benzimidazole, 2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1-(2-(2-propynyloxy)ethyl)-, (E)-2-butenedioate (1:2)収率 60.8%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒
2 回

反応条件

温度
120 °C

実験手順

A mixture of 2-chloro-1-[2-(propargyloxy)ethyl]-benzimidazole (3.70 g) and N-methylhomopiperazine (9.00 g) is stirred at 120° C. for 5 hours. A 5% aqueous sodium hydroxide (50 ml) is added to the reaction mixture, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate and then concentrated. The residue is dissolved in a small amount of chloroform and subjected to column chromatography using silica gel (60 g), and then eluted with chloroform-methanol (10:1 by volume). The eluate is concentrated to give a pale yellow oily substance (1.90 g). The pale yellow oily substance is dissolved in ethanol (3 ml) and the solution is added to a solution of fumaric acid (1.50 g) in hot ethanol (18 ml). After the mixture is allowed to cool, the precipitated crystals are separated by filtration and recrystallized from ethyl acetate-ethanol to give 1-[2-(propargyloxy)ethyl]-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate (2.14 g) as colorless needles, m.p. 122°-124.5° C.

後処理

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in a small amount of chloroform
  6. washeluted with chloroform-methanol (10:1 by volume)
  7. concentrationThe eluate is concentrated
  8. customto give a pale yellow oily substance (1.90 g)
  9. temperatureto cool
  10. customthe precipitated crystals are separated by filtration
  11. customrecrystallized from ethyl acetate-ethanol

出典と根拠

ORDレコード
ord-f680df1797c54fc7913bdc24bacf960a
出典データセット
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04430343

反応ノート

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