Anthranilic Acid → 2-Amino-N-cyclohexylbenzamide

HRID 1520336Notes

Reaction equation

HRID 1520336 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N=C=N.[NH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[NH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:16]

Participants

7

Reactant 5

HCID 227Anthranilic AcidHCID 7965CyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 160435Carbodiimide

Product 1

HCID 5776612-Amino-N-cyclohexylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a dry reaction vial was added cyclohexylamine (40 uμmol, 1.0 eq) and PS-carbodiimide resin (72 μmol, 1.8 eq). The solution of 2-amino-benzoic acid (44 μmol, 1.1 eq), diisopropyl ethyl amine (10 μLl) and HOBt (44 μmol, 1.1 eq) in THF (500 μL) was added to the above vial. The reaction mixture was heated at 40° C. for 6 h on a shaker. The resin was removed by filtration and washed with 10% MeOH/CH2Cl2. The solvent was removed in vacuo and the residue was applied to solid phase extraction cartridge (basic silica, 200 mg) and eluted with 50% EtOAc/CH2Cl2. After removal of the solvents, the crude 2-amino-N-cyclohexyl-benzamide was obtained and used for the following reaction.

Workup

  1. customTo a dry reaction
  2. customThe resin was removed by filtration
  3. washwashed with 10% MeOH/CH2Cl2
  4. customThe solvent was removed in vacuo
  5. extractionthe residue was applied to solid phase extraction cartridge (basic silica, 200 mg)
  6. washeluted with 50% EtOAc/CH2Cl2
  7. customAfter removal of the solvents

Sources & evidence

ORD record
ord-c63b5ff8d9c24fc39ed1ab91ef0cf027
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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