Benzoyl chloride → (R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

HRID 1689954Notes

Reaction equation

HRID 1689954 reaction equation
[Cl:1][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][CH2:14][C@H:13]2[CH3:18])=[N:4][N:3]=1.C(N(CC)C(C)C)(C)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][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][N:15]([C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:35])[CH2:14][C@H:13]2[CH3:18])=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 57581473(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine

Product 1

HCID 57581487(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine (2.94 g, 11.94 mmol) was dissolved in dry DMF (24 mL) and N,N-diisopropylethylamine (3.12 mL, 17.9 mmol). Benzoyl chloride (1.43 mL, 12.3 mmol) was added dropwise and the reaction stirred at rt for 16 hours. The reaction was taken up in ethyl acetate (200 mL), and washed with aqueous K2CO3 (10%), water, and then saturated sodium chloride. The organic phase was dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-70% ethyl acetate gave an off-white solid. MS (M+H)+=367.

Workup

  1. washwashed with aqueous K2CO3 (10%), water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-21448d06d95e4bb3b4ebe30b50cbe2bc
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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