Water → HCID 44212576, compound

HRID 1075540Notes

Reaction equation

HRID 1075540 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][C:19]=1[CH3:25].[OH2:26].Cl[CH2:28]Cl>>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:28]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N:10]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)[CH:5]=2)=[O:26])=[CH:20][C:19]=1[CH3:25]

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 233594-Bromo-3-methylanilineHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 44212576HCID 44212576, compoundYield 68%

Procedure

4Methoxy-3-(4-methyl-1-piperazinyl)benzeneamine (EP 0 533 267 A1) was added to a stirred solution of 1,1-carbonyldiimidazole (0.242 g, 1.49 mmol) in dichloromethane (20 ml). After 0.5 h, the reaction mixture was evaporated under reduced pressure and redissolved in dimethylformamide (10 ml). The resultant mixture was then treated with 4-bromo-3-methylaniline (0.253 g, 1.36 mmol), and stirred at room temperature overnight. Water (35 ml) was then added and the resultant precipitate was filtered off and dried in vacuo to give the title compound as a pale brown solid (0.400 g, 68%).

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. dissolutionredissolved in dimethylformamide (10 ml)
  3. filtrationthe resultant precipitate was filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1479456d311a4f84acf2a2da754f5547
Source dataset
uspto-grants-1999_05
Patent number
US05905080

Reaction notes

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