Benzoyl chloride → 1-(3,3-Dimethylpiperazin-1-yl)-4-phenylphthalazine

HRID 1689946Notes

Reaction equation

HRID 1689946 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][NH:15][C:14]([CH3:19])([CH3:18])[CH2:13]2)=[N:4][N:3]=1.C(N(CC)CC)C.C(Cl)(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl.C(OCC)(=O)C>[CH3:18][C:14]1([CH3:19])[NH:15][CH2:16][CH2:17][N:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:3][N:4]=2)[CH2:13]1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 575814821-Chloro-4-(3,3-dimethylpiperazin-1-yl)phthalazine

Product 1

HCID 669047751-(3,3-Dimethylpiperazin-1-yl)-4-phenylphthalazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-chloro-4-(3,3-dimethylpiperazin-1-yl)phthalazine (540 mg, 2 mmol) in 10 mL of dichloromethane was added triethylamine (0.56 mL, 4 mmol, 2 eq), followed by benzoyl chloride (0.26 mL, 2.2 mmol, 1.1 eq). The reaction was stirred at rt for 30 min and diluted with 100 mL of ethyl acetate. The organic layer was washed with 1×10 mL of sat. NaHCO3 solution and 1×10 mL of sat. NaCl solution. Purification by column chromatography (100:2 dichloromethane:methanol) afforded 1-(3,3-dimethylpiperazin-1-yl)-4-phenylphthalazine (BSL-7). 1H-NMR (400 Mhz) δ 1.65 (s, 6H), 3.46 (s, 2H), 3.63 (m, 4H), 7.34 (m, 3H), 7.42 (m, 3H), 7.42 (m, 3H), 7.83 (m, 2H), 8.03 (m, 1H), 8.17 (m, 1H).

Workup

  1. washThe organic layer was washed with 1×10 mL of sat. NaHCO3 solution and 1×10 mL of sat. NaCl solution
  2. customPurification by column chromatography (100:2 dichloromethane:methanol)

Sources & evidence

ORD record
ord-1c2e37f7cb244581bd4fb60cbaad75b4
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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