4-(3,5-Dimethylpiperazin-1-yl)aniline → HCID 178429948, compound

HRID 2236669Notes

Reaction equation

HRID 2236669 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[CH3:17][CH:18]1[NH:23][CH:22]([CH3:24])[CH2:21][N:20]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:19]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:31][C:28]1[CH:27]=[CH:26][C:25]([N:20]2[CH2:19][CH:18]([CH3:17])[NH:23][CH:22]([CH3:24])[CH2:21]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 176054784-(3,5-Dimethylpiperazin-1-yl)anilineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178429948HCID 178429948, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

An amount of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.5 g, 1.77 mmol) in 5 mL of N,N′-dimethylformamide is added [4-(3,5-dimethylpiperazin-1-yl)phenyl]amine (0.44 g, 2.13 mmol). The mixture reaction is stirred at 100° C. for 3 h. Mass spectroscopy suggested the completion of reaction. Solvent is subsequently evaporated under high-pressure vacuum to brown solid. The solid is stirred in ether, filtered and washed with a small amount of methanol, excess amount of ether and hexane, and dried in oven overnight to give 0.65 g (80.0% yield) of yellow solid:

Workup

  1. customThe mixture reaction
  2. customthe completion of reaction
  3. customSolvent is subsequently evaporated under high-pressure vacuum to brown solid
  4. stirringThe solid is stirred in ether
  5. filtrationfiltered
  6. washwashed with a small amount of methanol, excess amount of ether and hexane
  7. customdried in oven overnight

Sources & evidence

ORD record
ord-d678616dddd94a4caf5d278bfa1bd5ce
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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