Potassium Carbonate → 1-Benzyl-4-(4-chlorophthalazin-1-yl)piperazin-2-one

HRID 1689962Notes

Reaction equation

HRID 1689962 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.[CH2:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[O:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>C(OCC)(=O)C>[CH2:13]([N:20]1[CH2:25][CH2:24][N:23]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([Cl:12])=[N:4][N:3]=2)[CH2:22][C:21]1=[O:26])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 784901,4-DichlorophthalazineHCID 15143031-Benzylpiperazin-2-one

Product 1

HCID 575815501-Benzyl-4-(4-chlorophthalazin-1-yl)piperazin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,4-dichlorophthalazine (500 mg, 2.51 mmol), 1-benzylpiperazin-2-one (526 mg, 2.76 mmol), potassium carbonate (521 mg, 3.01 mmol), and N-methylpyrrolidinone (3 mL) were heated at 110° for 8 hours. The reaction was taken up in ethyl acetate (80 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give an orange oil. Chromatography over silica gel with a gradient of hexanes/0-40% ethyl acetate gave an off-white solid. MS (M+H)+=353.9.

Workup

  1. washwashed with aqueous K2CO3 (10%), water, and saturated sodium chloride
  2. dry with materialThe organics were dried (MgSO4)
  3. customevaporated
  4. customto give an orange oil

Sources & evidence

ORD record
ord-0cf0419d1a8246daac2d23fcbb6ebbc5
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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