1,4-Dichlorophthalazine → HCID 86627843, compound

HRID 1689943Notes

Reaction equation

HRID 1689943 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[N:4][N:3]=1.[CH3:13][C@H:14]1[CH2:19][NH:18][C@H:17]([CH3:20])[CH2:16][NH:15]1>ClCCl>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:15]2[CH2:16][C@@H:17]([CH3:20])[NH:18][CH2:19][C@@H:14]2[CH3:13])=[N:3][N:4]=1

Participants

4

Reactant 2

HCID 784901,4-DichlorophthalazineHCID 2206722,5-Dimethylpiperazine, trans-

Product 1

HCID 86627843HCID 86627843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

1,4-dichlorophthalazine (1.0 g, 5 mmole) and trans-2,5-dimethyl piperazine were combined in a reaction vial and heated to 130° C. for 3 h with stirring. After cooling to room temperature, the solid residue was dissolved in 150 mL of dichloromethane and washed with 1×20 mL of 1:1 saturated NaHCO3 solution:H2O and 1×20 mL of saturated NaCl solution. The organic phase was dried over MgSO4, filtered, and concentrated. Purification by column chromatography (100:5:1 dichloromethane:methanol:triethylamine) afforded 1-chloro-4-(trans-2,5-dimethylpiperazin-1-yl)phthalazine. MS (M+H)+=277.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 1×20 mL of 1:1 saturated NaHCO3 solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (100:5:1 dichloromethane:methanol:triethylamine)

Sources & evidence

ORD record
ord-d3f224c7e3bd4cdea1f873fc8f9fa419
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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