Water → HCID 18466731, compound

HRID 378384Notes

Reaction equation

HRID 378384 reaction equation
[CH3:1][CH:2]([C:4](=O)[C:5](=O)[CH:6]([CH3:8])[CH3:7])[CH3:3].[CH:11]1([NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[NH2:17].[OH2:19]>C(O)(=O)C>[CH:2]([C:4]1[C:5]([CH:6]([CH3:8])[CH3:7])=[N:18][C:11]2[CH2:16][CH2:15][CH2:14][C:13](=[O:19])[C:12]=2[N:17]=1)([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 46101,2-DiaminocyclohexaneHCID 1382173,4-Hexanedione, 2,5-dimethyl-

Product 1

HCID 18466731HCID 18466731, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.7 g of 2,5-dimethyl-3,4-hexanedione and 11.2 ml of 1,2-cyclohexanediamine were dissolved in 20 ml of acetic acid. The obtained solution was heated under reflux for 30 hours, cooled by allowing to stand, and poured into water, followed by the extraction with ethyl acetate. The organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and concentrated in a vacuum. The obtained residue was purified by silica gel chromatography (developer: 5% ethyl acetate/hexane) to give 6.8 g of the title compound as a colorless oil.

Workup

  1. temperatureThe obtained solution was heated
  2. temperatureunder reflux for 30 hours
  3. temperaturecooled
  4. extractionfollowed by the extraction with ethyl acetate
  5. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in a vacuum
  8. customThe obtained residue was purified by silica gel chromatography (developer: 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-feb076b8cf274b8ba57790a7191ec48e
Source dataset
uspto-grants-2000_02
Patent number
US06030964

Reaction notes

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