Carbon Dioxide → HCID 45595268, compound

HRID 1588086Notes

Reaction equation

HRID 1588086 reaction equation
[CH3:1][C@H:2](C(O)=O)[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.C([N:20](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[ClH:42].C(=O)=O>C1C=CC=CC=1.O>[ClH:42].[CH3:14][O:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:12]=[C:3]([CH:2]([NH2:20])[CH3:1])[CH:4]=[CH:5]2

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 156391NaproxenHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 45595268HCID 45595268, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A further representative compound of the present invention was prepared according to Scheme 1 in the following manner. To a solution of naproxen (10.0 g, 0.04 mole) in 50 mL benzene at room temperature were added triethylamine (6.1 mL, 0.04 mole) and diphenylphosphoryl azide (9.4 mL, 0.04 mole). The solution was heated to reflux and stirred for two hours before slowly adding concentrated HCl solution (12 M; 7.2 mL, 0.08 mole) via pipet. Evolution of CO2 gas was noted. The mixture was stirred at reflux for thirty minutes, then cooled to room temperature and concentrated in vacuo. Ether was added and the solution was concentrated again. A white solid precipitate was filtered and washed with ether to give 15.4 g of crude salt. Approximately 5.0 g of the salt was then placed in water and an insoluble gum was filtered off. The aqueous layer was basified with 2N NaOH solution and extracted with ethyl acetate (3×50 mL). The organic extract was washed with brine and dried (MgSO4), filtered and concentrated in vacuo to give 2.51 g of the 1-(6-methoxynaphthalen-2-yl)ethyl amine hydrochloride salt 2.1 as a white solid.

Workup

  1. customA further representative compound of the present invention was prepared
  2. temperatureThe solution was heated
  3. temperatureto reflux
  4. stirringThe mixture was stirred
  5. temperatureat reflux for thirty minutes
  6. concentrationconcentrated in vacuo
  7. additionEther was added
  8. concentrationthe solution was concentrated again
  9. filtrationA white solid precipitate was filtered
  10. washwashed with ether
  11. customto give 15.4 g of crude salt
  12. filtrationan insoluble gum was filtered off
  13. extractionextracted with ethyl acetate (3×50 mL)
  14. extractionThe organic extract
  15. washwas washed with brine
  16. dry with materialdried (MgSO4)
  17. filtrationfiltered
  18. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02cfebe78f7940918432b9314d1c7122
Source dataset
uspto-grants-1993_06
Patent number
US05220059

Reaction notes

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