Water → HCID 15925646, compound

HRID 654070Notes

Reaction equation

HRID 654070 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH3:19])=[C:9]1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.ClCCl.O.C[N:33](C)C=O>>[NH2:33][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH3:19])=[C:9]1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 159256341-(6-Bromohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

Product 1

HCID 15925646HCID 15925646, compound

Procedure

8.0 mmol of 1-(6-bromohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl indole and 8.8 mmol of phthalamidepotassium are heated in 100 ml of anhydrous dimethylformamide for 2 hours under reflux. Following cooling the product is shaken with dichloromethane and H2O. The product is then dried over Na2SO4 and the solvent distilled off. The residue is chromatographed on silica gel with dichloromethane. To liberate the amine the so-obtained colorless crystals are taken up in 50 ml of ethanol (99%) and mixed with hydrazine hydrate in 20 ml of ethanol. The mixture is now heated for 2 hours under reflux; after cooling, it is acidified with 40 ml of 2N HCl solution and suctioned off from the precipitate. After distilling off the solvent the mixture is made alkaline with 40 ml of 2N NaOH and extracted three times with ethyl acetate. The mixture is then dried over Na2SO4 and chromatographed on silica gel with dichloromethane/ethyl acetate (10:1, volume/volume). A viscous colorless to yellowish oil is obtained.

Workup

  1. temperatureunder reflux
  2. temperatureFollowing cooling the product
  3. dry with materialThe product is then dried over Na2SO4
  4. distillationthe solvent distilled off
  5. customThe residue is chromatographed on silica gel with dichloromethane
  6. additionmixed with hydrazine hydrate in 20 ml of ethanol
  7. temperatureThe mixture is now heated for 2 hours
  8. temperatureunder reflux
  9. temperatureafter cooling
  10. distillationAfter distilling off the solvent the mixture
  11. extractionextracted three times with ethyl acetate
  12. dry with materialThe mixture is then dried over Na2SO4
  13. customchromatographed on silica gel with dichloromethane/ethyl acetate (10:1, volume/volume)
  14. customA viscous colorless to yellowish oil is obtained

Sources & evidence

ORD record
ord-a183b675b6414465bf2867d383f8ad78
Source dataset
uspto-grants-1992_07
Patent number
US05130308

Reaction notes

Loading…