Potassium Carbonate → HCID 68455771, compound

HRID 2357569Notes

Reaction equation

HRID 2357569 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][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.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:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]1)=[N:7][N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 68455771HCID 68455771, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-bromo-1-chlorophthalazine (Example 1, 0.12 g, 0.5 mmol), 1-methylpiperazine (0.11 mL, 1.0 mmol) and potassium carbonate (0.07 g, 0.5 mmol) in 5 mL acetonitrile was added to a glass microwave reaction vessel. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 180° C. for about 20 min. After about 20 min. all starting material was converted to product (M+1=307, 309). The mixture was concentrated under vacuum and purified via flash chromatography (silica gel) eluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2M ammonia in MeOH/DCM to give (0.14 g) 6-bromo-1-(4-methylpiperazin-1-yl)phthalazine as a yellow solid. Found MS (ES+): 307, 309(M+H)+.

Workup

  1. additionwas added to a glass microwave reaction vessel
  2. concentrationThe mixture was concentrated under vacuum
  3. custompurified via flash chromatography (silica gel)
  4. washeluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2M ammonia in MeOH/DCM

Sources & evidence

ORD record
ord-c9932d5d079d49cf88582b2521bf274d
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

Loading…