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

HRID 1851813Notes

Reaction equation

HRID 1851813 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

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 under ice-cooling, and the mixture was stirred at room temperature overnight. After the ether layer was separated, the aqueous layer was neutralized with 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. temperaturecooling
  2. customAfter the ether layer was separated
  3. temperaturecooling
  4. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-602d1ebbf1284379bd44b288a3b84296
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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