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

HRID 572826
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 572826
[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
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Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7964ChlorobenzeneLösungsmittel
HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Versuchsvorschrift

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 hydroxide 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.

Aufarbeitung

  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 hydroxide 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

Quellen und Nachweise

ORD-Eintrag
ord-323791cb087e43e78a7fe0a38220c80e
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029357B2

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