Water → HCID 18466766, compound

HRID 1601008Notes

Reaction equation

HRID 1601008 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4](=O)[C:3]1=O.[CH:13]1([NH2:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[NH2:19].O>C(O)(=O)C>[CH3:1][C:2]1([CH3:12])[C:3]2[C:4](=[N:19][C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:13]=3[N:20]=2)[C:5]([CH3:9])([CH3:8])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 46101,2-DiaminocyclohexaneHCID 1407331,2-Cyclohexanedione, 3,3,6,6-tetramethyl-

Product 1

HCID 18466766HCID 18466766, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

20.0 g of 3,3,6,6,-tetramethyl-1,2-cyclohexanedione and 20 ml of 1,2-cyclohexanediamine were dissolved in 20 ml of acetic acid. The obtained solution was heated under reflux for 6 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 16.0 g of the title compound as a colorless oil.

Workup

  1. temperatureThe obtained solution was heated
  2. temperatureunder reflux for 6 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-e164ca0c5c6044188335e1451a39493c
Source dataset
uspto-grants-1999_11
Patent number
US05977125

Reaction notes

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