Cyclohexanecarboxylic acid → N-(3-Aminophenyl)cyclohexanecarboxamide

HRID 2376151Notes

Reaction equation

HRID 2376151 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[CH:9]1([C:15](O)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[NH2:7][C:3]1[CH:2]=[C:1]([NH:8][C:15]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:16])[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7413Cyclohexanecarboxylic acidHCID 7935M-PhenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 16772854N-(3-Aminophenyl)cyclohexanecarboxamideYield 54.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of m-phenylenediamine (2.00 g), cyclohexanecarboxylic acid (2.37 g), HOBt (2.75 g) and EDCI (3.9 g) in DMF (20 mL) was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with water and the resulting solid was collected by filtration. The solid was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/2 v/v) to give N-(3-aminophenyl)cyclohexanecarboxamide (2.2 g) as a white powder.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. customThe solid was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/2 v/v)

Sources & evidence

ORD record
ord-928aa6d2f8004723a302bab4a3d92639
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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