Sodium Carbonate → 2-(1-(2-(4-(1-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-1-methylethyl)phenyl)ethyl)-4-piperidinyl)-1-(2-ethoxyethyl)-1H-benzimidazole

HRID 384014Notes

Reaction equation

HRID 384014 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)([CH3:12])[CH3:11])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:26]([O:28][CH2:29][CH2:30][N:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)[CH3:27]>CO>[CH3:18][C:16]1([CH3:19])[CH2:15][O:14][C:13]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:43]3[CH2:44][CH2:45][CH:40]([C:32]4[N:31]([CH2:30][CH2:29][O:28][CH2:26][CH3:27])[C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=5[N:33]=4)[CH2:41][CH2:42]3)=[CH:5][CH:6]=2)([CH3:12])[CH3:11])=[N:17]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 138083611-(2-ethoxyethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazoleHCID 668698762-{1-[4-(2-Chloro-ethyl)-phenyl]-1-methyl-ethyl}-4,4-dimethyl-4,5-dihydro-oxazole

Product 1

HCID 404670312-(1-(2-(4-(1-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-1-methylethyl)phenyl)ethyl)-4-piperidinyl)-1-(2-ethoxyethyl)-1H-benzimidazoleYield 125.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a reaction vessel, 2-{1-[4-(2-chloro-ethyl)-phenyl]-1-methyl-ethyl}-4,4-dimethyl-4,5-dihydro-oxazole (1.9 g) prepared in the Example 9, sodium carbonate (0.8 g), 1-(2-ethoxyethyl)-2-piperidin-4-yl-1H-benzoimidazole (2.0 g) prepared in the Example 12 and methyl alcohol (20 mL) were introduced, and the mixture was reacted for 14 hours under reflux condition to obtain 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-1-methyl-ethyl]-phenyl}-ethyl)-piperidin-4-yl]-1-(2-ethoxy-ethyl)-1H-benzoimidazole (4.4 g, yield 87%, HPLC purity 98% or more).

Workup

  1. additionwere introduced
  2. customthe mixture was reacted for 14 hours
  3. temperatureunder reflux condition

Sources & evidence

ORD record
ord-fed0734555114617b1b79c4857ef0e86
Source dataset
uspto-grants-2013_02
Patent number
US08367704B2

Reaction notes

Loading…