Triethylamine → HCID 19364510, compound

HRID 1457732Notes

Reaction equation

HRID 1457732 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH:9](O)[CH3:10])=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C([N:34](CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH:9]([NH2:34])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19364481HCID 19364481, compound

Product 1

HCID 19364510HCID 19364510, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

141 mg of the alcohol compound thus obtained was dissolved in 2 ml of ethyl acetate, and 62 μl of methanesulfonyl chloride and 161 μl of triethylamine were added thereto, followed by stirring at room temperature for 30 minutes. Insoluble precipitates were filtered off from the reaction solution. Then, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 5 ml of dimethylformamide. Then, 255 mg of sodium azide was added thereto, followed by heating at 80° C. for 4 hours. The reaction solution was left to cool to room temperature. Then, ethyl ether and water were added thereto for extraction. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was heated and refluxed together with 187 mg of triphenylphosphine in 7 ml of 10%-water containing tetrahydrofuran for one hour. The reaction solution was evaporated to dryness under reduced pressure. Then, the residue was dissolved in ethanol and again evaporated to dryness under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=50/1→10/1) to obtain 129 mg (yield: 92%) of (1RS, 2SR)-2-(4-chlorophenyl)-1-methyl-3-(4-phenylethynylphenyl)propylamine.

Workup

  1. customInsoluble precipitates
  2. filtrationwere filtered off from the reaction solution
  3. concentrationThen, the filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 5 ml of dimethylformamide
  5. additionThen, 255 mg of sodium azide was added
  6. temperatureby heating at 80° C. for 4 hours
  7. waitThe reaction solution was left
  8. temperatureto cool to room temperature
  9. additionThen, ethyl ether and water were added
  10. extractionfor extraction
  11. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationThe drying agent was filtered off
  14. distillationthe solvent was distilled off under reduced pressure
  15. temperatureThe residue was heated
  16. temperaturerefluxed together with 187 mg of triphenylphosphine in 7 ml of 10%-water
  17. additioncontaining tetrahydrofuran for one hour
  18. customThe reaction solution was evaporated to dryness under reduced pressure
  19. dissolutionThen, the residue was dissolved in ethanol
  20. customagain evaporated to dryness under reduced pressure
  21. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=50/1→10/1)

Sources & evidence

ORD record
ord-c5e148e324a642139b0d5180aec8b1cd
Source dataset
uspto-grants-1998_12
Patent number
US05849747

Reaction notes

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