Ethylenediamine → 1-(2-Imidazolin-2-YL)-6-methoxy-5-methylindane

HRID 2220166Notes

Reaction equation

HRID 2220166 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[C:12]#[N:13])=[CH:5][C:4]=1[CH3:14].[CH2:15](N)[CH2:16][NH2:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>[NH:13]1[CH2:15][CH2:16][N:17]=[C:12]1[CH:9]1[C:10]2[C:6](=[CH:5][C:4]([CH3:14])=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6101p-Toluenesulfonic acidHCID 450914056-Methoxy-5-methyl-2,3-dihydro-1H-indene-1-carbonitrile

Product 1

HCID 117013911-(2-Imidazolin-2-YL)-6-methoxy-5-methylindaneYield 70.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 2.4 grams (0.013 mole) of 6-methoxy-5-methylindanecarbonitrile (iv) and 11.2 grams (0.045 mole) of the ethylenediamine salt of p-toluenesulfonic acid was stirred and heated to about 140° C.-160° C. where it was maintained for about 4.5 hours. The reaction mixture was then cooled to ambient temperature and dissolved in a mixture of aqueous 5% potassium carbonate and methylene chloride. The organic layer was removed, and the aqueous layer was extracted with two portions of methylene chloride. The combined extracts and organic layer were washed with one portion of aqueous 5% potassium carbonate. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a solid residue. The residue was purified by column chromatography on Grade II basic alumina (3% water) using mixtures of methylene chloride and methanol as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding about 2.1 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureheated to about 140° C.-160° C. where it
  2. temperaturewas maintained for about 4.5 hours
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted with two portions of methylene chloride
  5. washThe combined extracts and organic layer were washed with one portion of aqueous 5% potassium carbonate
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a solid residue
  9. customThe residue was purified by column chromatography on Grade II basic alumina (3% water)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8550e68e3c14b838d51b85796fb18c5
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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