Benzoyl chloride → HCID 46871827, compound

HRID 1689950Notes

Reaction equation

HRID 1689950 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10][N:9]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl.C(OCC)(=O)C>[CH3:1][C@H:2]1[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][N:9]=2)[CH2:4][CH2:5][N:6]([C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:38])[CH2:7]1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57581524HCID 57581524, compound

Product 1

HCID 46871827HCID 46871827, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-1-(2-methylpiperazin-1-yl)-4-phenylphthalazine (JK-10) (200 mg, 0.65 mmol) was dissolved in 5 mL of dichloromethane at room temperature. To this solution was added triethylamine (0.18 mL, 1.3 mmol, 2 eq) and benzoyl chloride (0.083 mL, 0.72 mmol, 1.1 eq). After 5 minutes, the reaction was diluted with 75 mL of ethyl acetate and washed with 5 mL of sat. NaHCO3, 5 mL of water, and 5 mL of brine. The organic phase was dried over MgSO4, filtered, and concentrated. Purification by column chromatography (35% ethyl acetate in hexanes) afforded 200 mg (75% yield) of (R)-(3-methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)(phenyl)methanone (4). MS (M+H)+=409.1

Workup

  1. washwashed with 5 mL of sat. NaHCO3, 5 mL of water, and 5 mL of brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-35f0e505495948c894e62ec892ab6c88
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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