Methanol → Ethyl 2-[4-(2-(4-(1-(2-ethoxyethyl)benzimidazole-2-yl)piperidine-1-yl)ethyl)phenyl]-2-methylpropanoate

HRID 451235Notes

Reaction equation

HRID 451235 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]OS(C)(=O)=O)=[CH:10][CH:9]=1)([CH3:7])[CH3:6])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:28]([O:30][CH2:31][CH2:32][N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[C:34]1[CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)[CH3:29].CO>O>[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:45]2[CH2:46][CH2:47][CH:42]([C:34]3[N:33]([CH2:32][CH2:31][O:30][CH2:28][CH3:29])[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=4[N:35]=3)[CH2:43][CH2:44]2)=[CH:10][CH:9]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 138083611-(2-ethoxyethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazoleHCID 866497982-[4-(2-Methanesulfonyloxy-ethyl)-phenyl]-2-methyl-propionic acid ethylester

Product 1

HCID 66869688Ethyl 2-[4-(2-(4-(1-(2-ethoxyethyl)benzimidazole-2-yl)piperidine-1-yl)ethyl)phenyl]-2-methylpropanoateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reaction vessel, 2-[4-(2-methanesulfonyloxy-ethyl)-phenyl]-2-methyl-propionic acid ethylester (3.2 g) prepared in the Example 8, sodium carbonate (1.1 g), 1-(2-ethoxyethyl)-2-piperidin-4-yl-1H-benzoimidazole (3.0 g) prepared in the Example 12 and methylalcohol (30 mL) were introduced, and the mixture was reacted for 14 hours under reflux condition. Distilled water (50 mL) was added thereto, and the mixture was stirred and crystallized. The crystals were filtered under reduced pressure, and washed with distilled water, and then dried to obtain 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzoimidazol-2-yl]-piperidin-1-yl}-ethyl)-phenyl]-2-methyl-propionic acid ethylester (4.5 g, yield 90%, HPLC purity 98.5% or more).

Workup

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

Sources & evidence

ORD record
ord-587178d117b9475ca461477881da9d49
Source dataset
uspto-grants-2013_07
Patent number
US08487106B2

Reaction notes

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