p-Toluenesulfonic acid → 1-(1-benzylpiperidin-4-yl)-5-methylsulphonyl-1H-benzimidazole

HRID 1592997Notes

Reaction equation

HRID 1592997 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=2[NH2:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)OC>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=3[N:25]=[CH:26]2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68704672N-(1-benzylpiperidin-4-yl)-2-amino-4-methylsulphonylaniline

Product 1

HCID 687092041-(1-benzylpiperidin-4-yl)-5-methylsulphonyl-1H-benzimidazoleYield 629.2%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

The crude material from step 2 (130 g) was stirred in 300 mL trimethylorthoformate containing 4-toluenesulphonic acid (8 g) at 90° C. for one hour, and collecting the methanol distillate. The reaction was cooled and filtered to give 108 g 1-(1-benzylpiperidin-4-yl)-5-methylsulphonyl-1H-benzimidazole as a brown solid.

Workup

  1. distillationcollecting the methanol distillate
  2. temperatureThe reaction was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-5e414ce351a742f7b04d66de323a4bcc
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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