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p-Toluenesulfonic acid → 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole

HRID 2404415
ノート
印刷プレビュー

反応式

HRID 2404415 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=1)[OH:11].O[CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1.CN1CCCC1=O>[Br:18][C:14]1[CH:13]=[C:12]([CH:10]([O:11][CH:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[CH:17]=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 660484-Piperidinol, 1-methyl-HCID 132601701H-benzimidazol-2-yl(3-bromophenyl)methanol

生成物 1

HCID 569479892-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole

試薬・触媒・溶媒 2

HCID 7964Chlorobenzene溶媒
HCID 13387
N-methyl-2-pyrrolidone
溶媒

実験手順

A mixture of 1H-benzimidazol-2-yl(3-bromophenyl)methanol (12.9 g), 4-hydroxy-1-methylpiperidine (4.86 g) and para-toluenesulfonic acid (24 g) in chlorobenzene (60 mL) and N-methylpyrrolidone (6 mL) is heated under reflux for 120 h in a Dean Stark apparatus. Solvent is removed by evaporation. To the residue is added water which is made alcaline by addition of sodium hydroxyde solution, then extracted with ethyl acetate. The pooled organic extracts are washed with water, treated with activated charcoal, dried over magnesium sulfate and concentrated under reduced pressure. The residue is triturated in diethyl ether to give 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole.

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 120 h in a Dean Stark apparatus
  3. customSolvent is removed by evaporation
  4. additionTo the residue is added water which
  5. additionby addition of sodium hydroxyde solution
  6. extractionextracted with ethyl acetate
  7. washThe pooled organic extracts are washed with water
  8. additiontreated with activated charcoal
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is triturated in diethyl ether

出典と根拠

ORDレコード
ord-d8a20bb094ba4bc48ea2d7048bafa9d4
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08802664B2

反応ノート

読み込み中…

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