1,2-Diaminocyclohexane, trans- → HCID 67794756, compound

HRID 892885Notes

Reaction equation

HRID 892885 reaction equation
C[O-].[Na+].[NH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH2:11].[C:12](OC)(=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C1C=CC=CC=1>[C:12]([NH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH2:11])(=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 438061,2-Diaminocyclohexane, trans-HCID 5364509Methyl OleateHCID 10942334Sodium Methoxide

Product 1

HCID 67794756HCID 67794756, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Sodium methoxide (0.60 g) was added to a solution of 1.14 g of trans-1,2-diaminocyclohexane and 2.96 g of methyl oleate in 15 ml of benzene, and the mixture was heated under reflux for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate-water. The organic layer was washed with saturated saline, and dried over anhydrous sodium sulfate. After drying it over anhydrous sodium sulfate, the residue obtained was purified by silica gel column chromatography to obtain 2.54 g of the objective compound (yield: 68%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate-water
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. dry with materialAfter drying it over anhydrous sodium sulfate
  9. customthe residue obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99255963a29544b683f5d5f07a1028ce
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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