Potassium Carbonate → 4-(6-Bromophthalazin-1-yl)-3-methylpiperazin-2-one

HRID 2357674Notes

Reaction equation

HRID 2357674 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[CH3:13][CH:14]1[NH:19][CH2:18][CH2:17][NH:16][C:15]1=[O:20].C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:19]1[CH2:18][CH2:17][NH:16][C:15](=[O:20])[CH:14]1[CH3:13])=[N:7][N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 51066003-Methyl-2-ketopiperazineHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 684530974-(6-Bromophthalazin-1-yl)-3-methylpiperazin-2-oneYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
190 °C

Procedure

In three separate sealed tubes were placed a mixture of 6-bromo-1-chlorophthalazine (0.250 g, 1.03 mmol), 3-methylpiperazin-2-one (0.239 g, 2.09 mmol), K2CO3 (0.155 g, 1.12 mmol) and 5 mL of CH3CN. The three reactions were heated at 190° C. for 15 min in a microwave oven. The reaction mixtures were combined, concentrated onto silica gel and purified using flash chromatography eluting with 2M NH3 in MeOH/CH2Cl2 (0:1→1:19) to give 200 mg (60%) of an orange oil.

Workup

  1. customIn three separate
  2. customsealed tubes
  3. customThe reaction mixtures
  4. concentrationconcentrated onto silica gel
  5. custompurified
  6. washeluting with 2M NH3 in MeOH/CH2Cl2 (0:1→1:19)

Sources & evidence

ORD record
ord-d5d1e10686c64ea5904b85bc59a4df5b
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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