Potassium Hydroxide → tert-butyl 4-(1-(2-ethoxyethyl)-1H-benzo[d]iMidazol-2-yl)piperidine-1-carboxylate

HRID 384008Notes

Reaction equation

HRID 384008 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].CS(O[CH:30]([O:32][CH2:33][CH3:34])[CH3:31])(=O)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:31][CH2:30][O:32][CH2:33][CH3:34])[C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21640578HCID 21640578, compoundHCID 54672426tert-butyl 4-(1H-benzo[d]iMidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 54672427tert-butyl 4-(1-(2-ethoxyethyl)-1H-benzo[d]iMidazol-2-yl)piperidine-1-carboxylateYield 91.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a reaction vessel, 4-(1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.5 g) prepared in the Example 10, toluene (10 mL) and potassium hydroxide (0.8 g) were introduced, and temperature of the mixture was controlled to 50° C. or more. To the mixture, ethoxyethanol methane sulfonate (1.3 g) was added, and then, it was stirred at the same temperature until the reaction was completed. After the reaction was completed, distilled water (10 mL) was added to separate layers, and then an organic layer was condensed to obtain 4-[1-(2-ethoxyethyl)-1H-benzoimidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.7 g, 91%).

Workup

  1. additionwere introduced
  2. customwas controlled to 50° C. or more
  3. distillationdistilled water (10 mL)
  4. additionwas added
  5. customto separate layers
  6. customcondensed

Sources & evidence

ORD record
ord-c13caf32eb7443e7ac3460b454e2dea9
Source dataset
uspto-grants-2013_02
Patent number
US08367704B2

Reaction notes

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