1-Bromooctane → HCID 22132162, compound

HRID 1856620Notes

Reaction equation

HRID 1856620 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[C:21]([CH:22]=1)=[N:20][C:19]1[C:14](=[CH:15][CH:16]=[C:17]([NH2:23])[CH:18]=1)[CH:13]=2.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CS(C)=O>[CH2:25]([NH:23][C:17]1[CH:16]=[CH:15][C:14]2[C:19]([CH:18]=1)=[N:20][C:21]1[C:12](=[CH:11][CH:10]=[C:9]([NH:8][CH2:11][CH2:10][CH2:9][CH2:22][CH2:21][CH2:12][CH2:13][CH3:14])[CH:22]=1)[CH:13]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 197873Proflavin hydrochloride

Product 1

HCID 22132162HCID 22132162, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

6.33 g of anhydrous potassium carbonate are added to a solution of 2.5 g of 3,6-diaminoacridine hydrochloride and 3.55 ml of 1-bromooctane in 50 ml of dimethyl sulfoxide, and the mixture is stirred at 80° C. for 48 hours. The cooled reaction mixture is subsequently poured onto ice, and the brown suspension is extracted with methylene chloride. The organic phase is washed with saturated aqueous NaCl solution and dried over sodium sulfate. After evaporation, the red-brown oil is chromatographed on silica gel using methylene chloride/methanol (9:1). After evaporation of the solvent, the residue is taken up in diethyl ether/methanol (10:1) and chromatographed on aluminium oxide. The eluate is taken up in methanol, 2N HCl is added, the mixture is extracted with diethyl ether, and the ether phase is dried and evaporated. The residue is dissolved in methylene chloride, n-hexane is added, and the red crystalline precipitate formed is filtered off. Further product can be isolated from the mother liquor after evaporation. The melting point of the title compound is 245° C. Absorption spectrum (ethanol): λmax =472 nm; ε=51 400.

Workup

  1. customThe cooled reaction mixture
  2. additionis subsequently poured onto ice
  3. extractionthe brown suspension is extracted with methylene chloride
  4. washThe organic phase is washed with saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation
  7. customthe red-brown oil is chromatographed on silica gel
  8. customAfter evaporation of the solvent
  9. customchromatographed on aluminium oxide
  10. addition2N HCl is added
  11. extractionthe mixture is extracted with diethyl ether
  12. dry with materialthe ether phase is dried
  13. customevaporated
  14. dissolutionThe residue is dissolved in methylene chloride
  15. additionn-hexane is added
  16. customthe red crystalline precipitate formed
  17. filtrationis filtered off
  18. customFurther product can be isolated from the mother liquor
  19. customafter evaporation
  20. customis 245° C
  21. customAbsorption spectrum (ethanol)

Sources & evidence

ORD record
ord-4bccfc123855446692d996b62aaa8014
Source dataset
uspto-grants-2000_11
Patent number
US06143570

Reaction notes

Loading…