1,4-Dichlorophthalazine → Phthalazine

HRID 1689944Notes

Reaction equation

HRID 1689944 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][N:3]=1.C[C@H]1CNC[C@@H](C)N1>CC(CC(C)=O)C>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 784901,4-DichlorophthalazineHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 9207Phthalazine

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

1,4-dichlorophthalazine (1.6 g, 8 mmol) was slurried in 80 mL of MIBK and 2,6 cis-dimethyl piperazine (3.6 g, 32 mmol, 4 eq) was added. The reaction was stirred overnight and the solvent was removed in vacuo. The crude material was dissolved in 200 mL of CH2Cl2 and washed with 1×30 mL of a 1:1 mixture of H2O and sat. sodium bicarbonate and 1×30 mL of sat. NaCl solution. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography (100:5:1 dichloromethane:methanol:triethylamine) afforded 1.6 g (72%) of 1-chloro-4-(cis)-3,5-dimethylpiperazin-1-yl)phthalazine. MS (M+H)+=277.1.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe crude material was dissolved in 200 mL of CH2Cl2
  3. washwashed with 1×30 mL of a 1:1 mixture of H2O and sat. sodium bicarbonate and 1×30 mL of sat. NaCl solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (100:5:1 dichloromethane:methanol:triethylamine)

Sources & evidence

ORD record
ord-1de3b88ff35842479dfa0c504deec53b
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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