p-Toluenesulfonic acid → HCID 56947989, compound

HRID 2404415Notes

Reaction equation

HRID 2404415 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 56947989HCID 56947989, compound

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d8a20bb094ba4bc48ea2d7048bafa9d4
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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