9-Chloroacridine → JP 1302

HRID 1357481Notes

Reaction equation

HRID 1357481 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl[C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[CH:28]=[CH:27][CH:26]=[CH:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2>Cl.CO>[CH:18]1[C:17]2[C:22](=[N:23][C:24]3[C:29]([C:16]=2[NH:12][C:11]2[CH:13]=[CH:14][C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[CH:9][CH:10]=2)=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 710139-ChloroacridineHCID 7372534-(4-Methylpiperazin-1-yl)aniline

Product 1

HCID 540335JP 1302Yield 12%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalyst2×HCID 887MethanolSolvent2×

Procedure

0.191 g (1.0 mmol) of 4-(4-methylpiperazin-1-yl)aniline, 2.5 ml of methanol and a few drops of concentrated hydrochloric acid were mixed and heated under reflux. The 9-chloroacridine (1-1,5 equivalents) and 2.5 ml methanol were mixed separately and added to the reaction mixture in small portions. After 30 min of stirring, two drops of concentrated hydrochloric acid were added, and heating was continued for 2 h. The reaction mixture was then evaporated to dryness and purified by chromatography (silica gel column; gradient from 100% methylene chloride to 90% methylene chloride and 10% methanol; when 4-(4-methylpiperazin-1-yl)aniline eluted from the column, the eluent was changed to methylene chloride:methanol:triethylamine 94:5:1). A final amount of 0.126 g (34%, overall yield 12%) of the title compound in pure form was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. additionadded to the reaction mixture in small portions
  4. temperatureheating
  5. waitwas continued for 2 h
  6. customThe reaction mixture was then evaporated to dryness
  7. custompurified by chromatography (silica gel column
  8. washwhen 4-(4-methylpiperazin-1-yl)aniline eluted from the column

Sources & evidence

ORD record
ord-08d96c4dc0cd421ea386a7a703aa21a0
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

Loading…