Sodium Carbonate → 1-benzyl-4-((S)-3-methyl-piperazin-1-yl)-phthalazine

HRID 42178

Reaction equation

HRID 42178 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 27342192-Methylpiperazine, (S)-HCID 64045661-Benzyl-4-chlorophthalazine

Product 1

HCID 441864791-benzyl-4-((S)-3-methyl-piperazin-1-yl)-phthalazineYield 64.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Solid Na2CO3 (400 mg, 3.8 mmol, 3.8 eq) is added to a solution of 1-benzyl-4-chlorophthalazine (250 mg, 0.98 mmol, 1 eq) and (5)-2-methyl-piperazine (400 mg, 4.0 mmol, 4.0 eq) in dioxane (5 mL). The resulting suspension is heated at 100° C. for 48 h. The reaction mixture is concentrated, EtOAc (50 mL) and water (15 mL) are added. 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 (200 mg, 64% yield).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionEtOAc (50 mL) and water (15 mL) are added
  3. washThe organic fraction washed with water
  4. dry with materialbrine, then is dried over sodium sulfate
  5. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-027bcfb2f02b474e89a07d6e5c810596
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

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