Cyclohexene → HCID 23104593, compound

HRID 734146Notes

Reaction equation

HRID 734146 reaction equation
[OH:1][CH2:2][C:3]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)([CH2:6][OH:7])[CH2:4][OH:5].C1CCCCC=1>[Pd].O>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:3]([CH2:4][OH:5])([CH2:6][OH:7])[CH2:2][OH:1])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 23104606HCID 23104606, compound

Product 1

HCID 23104593HCID 23104593, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

7.3 g (0.03 mol) of 2-hydroxymethyl-2-(4-nitrophenylamino)propane-1,3-diol (5) were placed in a mixture of alcohol, water, and cyclohexene in proportions of 30 ml/15 ml/3 ml. 3 g of 10% Pd/C catalyst were added and the mixture was refluxed for 2 hours until decolorized. The medium was filtered while hot and the catalyst was washed with alcohol. The filtrate was concentrated to dryness and then taken up in 10 ml of ethanol, and the precipitate formed was filtered off and washed with alcohol and then with isopropyl ether. After drying, 3.7 g of a white powder were obtained, the elemental analysis of which gave the following results:

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. filtrationThe medium was filtered while hot and the catalyst
  3. washwas washed with alcohol
  4. concentrationThe filtrate was concentrated to dryness
  5. customthe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with alcohol
  8. customAfter drying

Sources & evidence

ORD record
ord-19cbb4b789a343518e5b2493daf66598
Source dataset
uspto-grants-2009_09
Patent number
US07591860B2

Reaction notes

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