Cesium carbonate → N,N-dimethylaminoethyl 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylate

HRID 1608489Notes

Reaction equation

HRID 1608489 reaction equation
Cl.O[C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[C:8]3[C:13](=[C:14]([C:17]([OH:19])=[O:18])[C:15]=2[CH:16]=1)[CH:12]=[C:11]1[CH:20]=[CH:21][CH:22]=[CH:23][C:10]1=[CH:9]3.[C:24](=[O:27])([O-])[O-].[Cs+].[Cs+].Br.[CH3:31][N:32]([CH2:34][CH2:35]Br)[CH3:33]>CS(C)=O>[CH3:31][N:32]([CH2:34][CH2:24][O:27][C:16]1[C:15]2[C:14]([C:17]([O:19][CH2:35][CH2:34][N:32]([CH3:33])[CH3:31])=[O:18])=[C:13]3[C:8]([CH:9]=[C:10]4[CH:23]=[CH:22][CH:21]=[CH:20][C:11]4=[CH:12]3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:33]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 457913472-Bromoethyldimethylammonium bromideHCID 867485242-Hydroxy-benz[b]acridine-12-carboxylic acid hydrochloride

Product 1

HCID 86748523N,N-dimethylaminoethyl 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylateYield 18%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2-hydroxy-benz[b]acridine-12-carboxylic acid hydrochloride (360 mg, 1,108 mmol) in methyl sulfoxide (11 ml) were added cesium carbonate (3.61 g, 11.08 mmol) and N,N-dimethylaminoethyl bromide hydrobromide (1.03 g, 4.432 mmol). After 15 hours of stirring at 60° C. under nitrogen, the reaction mixture was diluted with methyl sulfoxide (20 ml) and filtered to remove the insoluble impurities. The filtrate was concentrated under reduced pressure to a small volume, which was separated on a preparative-TLC plate (2 mm silica gel) by developing with chloroform/methanol/water (47:48:5). The desired orange band was collected and extracted with 25% methanol/chloroform. Removal of the solvents under reduced pressure gave N,N-dimethylaminoethyl 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylate (86 mg, 18%). Rf 0.6 (silica gel, chloroform/methanol/water 65:25:4). MS (FAB, Glycerol Matrix): m/z 432 (M+1).

Workup

  1. filtrationfiltered
  2. customto remove the insoluble impurities
  3. concentrationThe filtrate was concentrated under reduced pressure to a small volume, which
  4. customwas separated on a preparative-TLC plate (2 mm silica gel)
  5. customThe desired orange band was collected
  6. extractionextracted with 25% methanol/chloroform
  7. customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record
ord-ff21bd7d959943589747264e147eb2e9
Source dataset
uspto-grants-1995_03
Patent number
US05395752

Reaction notes

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