1,4-Dichlorophthalazine → 1-Chloro-4-(3,3-dimethylpiperazin-1-yl)phthalazine

HRID 1689945Notes

Reaction equation

HRID 1689945 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:14]1([CH3:20])[CH2:19][NH:18][CH2:17][CH2:16][NH:15]1>CCC(C)=O.ClCCl>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:18]2[CH2:17][CH2:16][NH:15][C:14]([CH3:20])([CH3:13])[CH2:19]2)=[N:3][N:4]=1

Participants

5

Reactant 2

HCID 784901,4-DichlorophthalazineHCID 146641862,2-Dimethylpiperazine

Product 1

HCID 575814821-Chloro-4-(3,3-dimethylpiperazin-1-yl)phthalazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

1,4-dichlorophthalazine (1 g, 5 mmol) and 2,2-dimethyl piperazine (1.75 g, 15 mmol, 3 eq) were slurried in 5 mL of MEK for 3 h at 45° C. After cooling to rt, the reaction was diluted with 150 mL of dichloromethane and washed with 1×20 mL of sat. NaHCO3 and 1×20 mL of sat. NaCl solution. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography (100:5→8:1 dichloromethane:methanol:triethylamine) afforded 1-chloro-4-(3,3-dimethylpiperazin-1-yl)phthalazine. MS (M+H)+=277.0.

Workup

  1. washwashed with 1×20 mL of sat. NaHCO3 and 1×20 mL of sat. NaCl solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (100:5→8:1 dichloromethane:methanol:triethylamine)

Sources & evidence

ORD record
ord-0f30933ce1bd4ba3b9c48fb3a1bdb636
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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