HCID 68509815, compound → HCID 68509233, compound

HRID 1716563Notes

Reaction equation

HRID 1716563 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=3[N:14]=[C:13]2[CH:22]([CH3:24])[CH3:23])[CH:8]([O:25][CH3:26])[CH2:7]1)=O)C>[OH-].[K+].CCO>[CH:22]([C:13]1[N:12]([CH:9]2[CH2:10][CH2:11][NH:6][CH2:7][CH:8]2[O:25][CH3:26])[C:16]2[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=2[N:14]=1)([CH3:24])[CH3:23]

Participants

3

Reactant 1

HCID 68509815HCID 68509815, compound

Product 1

HCID 68509233HCID 68509233, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 21946426Potassium hydroxide ethanolSolvent

Procedure

A solution of 4-(2-isopropyl-5-methyl-benzoimidazol-1-yl)-3-methoxy-piperidine-1-carboxylic acid ethyl ester (465 mg, 1.37 mmol) in a 1/1 1N KOH/EtOH solution (10 mL) was heated to 80° C. overnight. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (15/1 CH2Cl2/CH3OH) to yield 2-isopropyl-1-(3-methoxy-piperidin-4-yl)-5-methyl-1H-benzoimidazole (69 mg, 18%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (15/1 CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-999142100e9a46bcaa0a8ad7abf4188d
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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