Sodium Carbonate → 1-Benzyl-4-((R)-3-methyl-piperazin-1-yl)-phthalazine

HRID 42177

Reaction equation

HRID 42177 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH2:7]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](Cl)=[N:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:25][C@@H:26]1[CH2:31][NH:30][CH2:29][CH2:28][NH:27]1>O1CCOCC1>[CH2:7]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([N:30]2[CH2:29][CH2:28][NH:27][C@H:26]([CH3:25])[CH2:31]2)=[N:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 64045661-Benzyl-4-chlorophthalazineHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 441862481-Benzyl-4-((R)-3-methyl-piperazin-1-yl)-phthalazineYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Solid Na2CO3 (200 mg, 1.9 mmol, 1.9 eq) is added to a solution of 1-benzyl-4-chlorophthalazine (250 mg, 0.98 mmol, 1 eq) and (R)-2-methyl-piperazine (400 mg, 4.0 mmol, 4.0 eq) in dioxane (5 mL) in a microwave vial. The vial is sealed and irradiated in the microwave at 150° C. (high absorption setting) for 30 minutes. The reaction mixture is filtered and concentrated, then diluted with EtOAc (50 mL) and water (15 mL). The organic fraction washed with water and then brine, then is dried over sodium sulfate. The solvent is evaporated under reduced pressure to afford the title compound as a white solid (180 mg, 58% yield).

Workup

  1. customThe vial is sealed
  2. customirradiated in the microwave at 150° C. (high absorption setting) for 30 minutes
  3. filtrationThe reaction mixture is filtered
  4. concentrationconcentrated
  5. additiondiluted with EtOAc (50 mL) and water (15 mL)
  6. washThe organic fraction washed with water
  7. dry with materialbrine, then is dried over sodium sulfate
  8. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-254f7c629db147839715ceb1129a9f43
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

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