1-Phenylpiperazine → HCID 24947219, compound

HRID 1667472Notes

Reaction equation

HRID 1667472 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[C:14]1([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC(N(C)C)=O.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([N:23]3[CH2:24][CH2:25][N:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:21][CH2:22]3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 70961-PhenylpiperazineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24947219HCID 24947219, compoundYield 15.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (100 mg, 0.385 mmol), 1-phenylpiperazine (0.064 mL, 0.424 mmol), Pd2(dba)3 (15 mg, 0.016 mmol), rac-BINAP (36 mg, 0.058 mmol) and NaOtBu (46 mg, 0.479 mmol) in DMA (3 mL) was heated in a microwave at 90° C. for 10 minutes. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(4-phenyl-piperazin-1-yl)-2H-phthalazin-1-one (20 mg) as an orange solid, 1H (400 MHz, d6-DMSO) δ: 3.32 (m, 4H), 3.61 (m, 4H), 6.81 (t, 1H), 7.00 (d, 2H), 7.15 (d, 1H), 7.24 (t, 2H), 7.62 (dd, 1H), 8.07 (d, 1H), 12.57 (s, 1H) ppm; m/z (M+1) 341.01.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

Sources & evidence

ORD record
ord-321f5440cdac4d5fa1640ea437cf6860
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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