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

HRID 2357582Notes

Reaction equation

HRID 2357582 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.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][C:14]1=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:16]1[CH2:17][CH2:18][NH:13][C:14](=[O:19])[CH2:15]1)=[N:7][N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 231360Piperazin-2-oneHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 684552784-(6-Bromophthalazin-1-yl)piperazin-2-oneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
190 °C

Procedure

A glass microwave reaction vessel was charged with 6-bromo-1-chlorophthalazine (Example 1, 0.11 g, 0.45 mmol), piperazin-2-one (0.090 g, 0.90 mmol), potassium carbonate (0.062 g, 0.45 mmol) and 5 mL acetonitrile. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 190° C. for about 12 min (watts, Powermax feature on, ramp time 1 min). The mixture was purified directly via flash chromatography (silica gel) eluting with 5% 2 M ammonia methanol/DCM to give the 4-(6-bromophthalazin-1-yl)piperazin-2-one (0.115 g) as a pale yellow solid. Found MS (ES+): 307, 309(M+H)+.

Workup

  1. customA glass microwave reaction vessel
  2. customThe mixture was purified directly via flash chromatography (silica gel)
  3. washeluting with 5% 2 M ammonia methanol/DCM

Sources & evidence

ORD record
ord-6a374d8e9a90413799d8eea059603c92
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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