Ethylenediamine → 2-[4,4-Diphenylcyclohexylamino]ethylamine

HRID 1976587Notes

Reaction equation

HRID 1976587 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([NH2:23])[CH2:21][NH2:22]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH:10]([NH:22][CH2:21][CH2:20][NH2:23])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 1382814,4-Diphenylcyclohexanone

Product 1

HCID 219986562-[4,4-Diphenylcyclohexylamino]ethylamineYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4,4-diphenylcyclohexanone (2.5 g) and ethylenediamine (10 g) and p-toluenesulfonic acid (100 mg) in benzene (200 mL) was refluxed for 4 h in Dean-Stark trap to remove the water that formed. Solvent was evaporated and the residue was redissolved in methanol (60 mL) and cooled to 0° C. To this, sodium borohydride (2 g) was added in portions and the mixture was stirred at room temperature for 3 h. Solvent was evaporated, the residue was dissolved in dichloromethane (300 mL), washed with brine (3×500 mL), dried (potassium carbonate), and the solvent evaporated to leave the product as a colorless viscous oil (2.94 g, 100%). The 1H-NMR showed this product to be pure and was used in the next step without any further purification.

Workup

  1. temperaturewas refluxed for 4 h in Dean-Stark trap
  2. customto remove the water
  3. customthat formed
  4. customSolvent was evaporated
  5. dissolutionthe residue was redissolved in methanol (60 mL)
  6. additionTo this, sodium borohydride (2 g) was added in portions
  7. customSolvent was evaporated
  8. dissolutionthe residue was dissolved in dichloromethane (300 mL)
  9. washwashed with brine (3×500 mL)
  10. dry with materialdried (potassium carbonate)
  11. customthe solvent evaporated

Sources & evidence

ORD record
ord-924edd878e674543a4b99b51a09ede99
Source dataset
uspto-grants-2001_05
Patent number
US06228861B1

Reaction notes

Loading…