Methanol → 2-(4-{2-[4-(1H-benzoimidazol-2-yl)-piperidin-1-yl]-ethyl}-phenyl)-2-methyl-propionic acid methylester

HRID 472802Notes

Reaction equation

HRID 472802 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14]OS(C)(=O)=O)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].C(=O)([O-])[O-].[Na+].[Na+].[NH:27]1[CH2:32][CH2:31][CH:30]([C:33]2[NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[N:34]=2)[CH2:29][CH2:28]1.CO>O>[CH3:1][O:2][C:3](=[O:20])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:27]2[CH2:28][CH2:29][CH:30]([C:33]3[NH:34][C:35]4[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=4[N:37]=3)[CH2:31][CH2:32]2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 7158102-(piperidin-4-yl)-1H-1,3-benzodiazoleHCID 452575292-[4-(2-Methanesulfonyloxy-ethyl)-phenyl]-2-methyl-propionic acid methylester

Product 1

HCID 452575302-(4-{2-[4-(1H-benzoimidazol-2-yl)-piperidin-1-yl]-ethyl}-phenyl)-2-methyl-propionic acid methylesterYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reaction vessel, 2-[4-(2-methanesulfonyloxy-ethyl)-phenyl]-2-methyl-propionic acid methylester (3.0 g) prepared in the Example 5, sodium carbonate (1.1 g), 2-(4-piperadinyl)-1H-benzoimidazole (3.0 g) and methylalcohol (30 mL) were introduced, and the mixture was reacted for 14 hours under reflux condition. Distilled water (50 mL) was added to crystallize. The crystals were filtered under reduced pressure, washed with distilled water, and dried to obtain 2-(4-{2-[4-(1H-benzoimidazol-2-yl)-piperidin-1-yl]-ethyl}-phenyl)-2-methyl-propionic acid methylester (3.4 g, yield 85%).

Workup

  1. additionwere introduced
  2. customthe mixture was reacted for 14 hours
  3. temperatureunder reflux condition
  4. customto crystallize
  5. filtrationThe crystals were filtered under reduced pressure
  6. washwashed with distilled water
  7. customdried

Sources & evidence

ORD record
ord-9c113441180e4825b6d4f1ec0c9d076c
Source dataset
uspto-grants-2014_01
Patent number
US08633223B2

Reaction notes

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