1-Aminocyclohexanecarboxylic acid → 1-[(4-Fluorobenzoyl)amino]cyclohexanecarboxylic acid

HRID 448740Notes

Reaction equation

HRID 448740 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>CCOCC.O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 13661-Aminocyclohexanecarboxylic acidHCID 10340Sodium CarbonateHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 246939621-[(4-Fluorobenzoyl)amino]cyclohexanecarboxylic acidYield 660.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Under ice-cooling, a solution of 25.0 g (15.8 mmol) of 4-fluorobenzoyl chloride in 30 ml of ether was added dropwise to a mixture solution of 22.6 g (15.8 mmol) of 1-aminocyclohexanecarboxylic acid and 25.0 g (23.7 mmol) of sodium carbonate in 100 ml of ether and 300 ml of water, and the mixture was stirred at room temperature overnight. After the ether layer was separated, the aqueous layer was neutralized by concentrated hydrochloric acid under ice-cooling, and the precipitated crystal was collected by filtration to obtain 27.7 g (66%) of the title compound.

Workup

  1. temperatureUnder ice-cooling
  2. customAfter the ether layer was separated
  3. temperaturecooling
  4. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-e1f7a8fffb6b4bdbbec4704afa3884a5
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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