Acridone → HCID 86741919, compound

HRID 986255Notes

Reaction equation

HRID 986255 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.Cl.Cl.[CH2:21]([N:23]([CH2:35][CH3:36])[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33]Cl)[CH2:28][CH2:27]1)[CH3:22]>CN(C)C=O>[CH2:35]([N:23]([CH2:21][CH3:22])[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][C:11]2[C:12]3[C:13](=[O:15])[C:14]4[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=4)[NH:6][C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH2:28][CH2:27]1)[CH3:36]

Participants

5

Reactant 3

HCID 2015AcridoneHCID 24758Sodium hydrideHCID 21254462HCID 21254462, compound

Product 1

HCID 86741919HCID 86741919, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9.75 g of 9-acridanone, 200 ml of dimethylformamide and 4.8 g sodium hydride is stirred for 0.5 hour, treated portionwise with 17.8 g of 2-[4-[2-(diethylamino)ethyl]-1-piperazinyl]ethyl chloride trihydrochloride, stirred at 70° for 18 hours, then heated to boiling under reflux for 8 hours and evaporated. The residue is treated with 100 ml of water and extracted with dichloromethane. The extract is washed with water, dried and evaporated. The product is crystallized twice from petroleum ether and there is obtained 10-[2-[4-[2-(diethylamino)ethyl]-1-piperazinyl]ethyl-9-acridanone of melting point 106°-108°.

Workup

  1. stirringstirred at 70° for 18 hours
  2. temperatureheated
  3. temperatureunder reflux for 8 hours
  4. customevaporated
  5. additionThe residue is treated with 100 ml of water
  6. extractionextracted with dichloromethane
  7. washThe extract is washed with water
  8. customdried
  9. customevaporated
  10. customThe product is crystallized twice from petroleum ether

Sources & evidence

ORD record
ord-c67e82c3bcc841a9bc54849d1ab54122
Source dataset
uspto-grants-1987_12
Patent number
US04711889

Reaction notes

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