Diethylene Glycol → 1,7-Diamino-3,5-dimethyladamantane

HRID 23826

Reaction equation

HRID 23826 reaction equation
C([NH:4][C:5]12[CH2:18][C:9]3([CH3:19])[CH2:10][C:11]([NH:14]C(=O)C)([CH2:13][C:7]([CH3:20])([CH2:8]3)[CH2:6]1)[CH2:12]2)(=O)C.C(O)COCCO>O>[NH2:4][C:5]12[CH2:18][C:9]3([CH3:19])[CH2:10][C:11]([NH2:14])([CH2:13][C:7]([CH3:20])([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

4

Reactant 2

HCID 8117Diethylene GlycolHCID 28424991,7-Diacetamido-3,5-dimethyladamantane

Product 1

HCID 129936571,7-Diamino-3,5-dimethyladamantaneYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diamide 3 (1.56 g) was added to diethyene glycol (25 mL). The reaction mixture was stirred at 175˜180° C. for 16 h. The brown solution was cooled to room temperature, and water was added (100 mL). The reaction mixture was extracted with a solvent consisting of ethyl acetate (80%) and t-butylmethyl ether (20%) (70 mL×7). The combined organic solvent was washed with water and brine, and dried over sodium sulfate. The solution was concentrated to approximately 20 mL. Anhydrous hydrogen chloride in ethyl acetate was added. The precipitate was filtered. The product was then dissolved in water (10 mL). The product was extracted with ethyl acetate (10 mL×6). Solvent was removed to afford diamine 4 as an off-white solid (767 mg).

Workup

  1. extractionThe reaction mixture was extracted with a solvent
  2. washThe combined organic solvent was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solution was concentrated to approximately 20 mL
  5. additionAnhydrous hydrogen chloride in ethyl acetate was added
  6. filtrationThe precipitate was filtered
  7. dissolutionThe product was then dissolved in water (10 mL)
  8. extractionThe product was extracted with ethyl acetate (10 mL×6)
  9. customSolvent was removed

Sources & evidence

ORD record
ord-97e03a5d5e264ac4af60378567430886
Source dataset
uspto-grants-2005_02
Patent number
US06852889B2

Linked notes

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