Water → 1-[(Benzoylamino)methyl]cyclohexanecarboxylic acid

HRID 1009921Notes

Reaction equation

HRID 1009921 reaction equation
[C:1]([NH:9][CH2:10][C:11]1([C:17]([O:19]CC)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O>C(O)C>[C:1]([NH:9][CH2:10][C:11]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57846990Ethyl 1-[(benzoylamino)methyl]cyclohexanecarboxylate

Product 1

HCID 178322521-[(Benzoylamino)methyl]cyclohexanecarboxylic acidYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-[(benzoylamino)methyl]cyclohexanecarboxylate (10.2 g, 35.1 mmol) in ethanol (50 ml) was added 50% aqueous potassium hydroxide solution (4 ml), and the mixture was heated under reflux for 6 hrs. Water (400 ml) was added and the reaction mixture was washed with diethyl ether. The aqueous layer was acidified (pH 2) with 5N hydrochloric acid, the precipitate was collected by filtration, washed with water and dried at 50° C. under reduced pressure. Recrystallization from ethanol-toluene gave the title compound (6.83 g, 74%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. washthe reaction mixture was washed with diethyl ether
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customdried at 50° C. under reduced pressure
  7. customRecrystallization from ethanol-toluene

Sources & evidence

ORD record
ord-e9f43d7980aa40c1bdaaed480f6a4600
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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