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Tetrafluoroboric acid → N-(3,4-Dichlorophenyl)-3-[2-(4-methylpiperazin-1-yl)phenyl]-acrylamide

HRID 1384464
Notes
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Reaction equation

HRID 1384464 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2N)[CH2:4][CH2:3]1.F[B-](F)(F)F.[H+].N([O-])=O.[Na+].[Cl:25][C:26]1[CH:27]=[C:28]([NH:33][C:34](=[O:37])[CH:35]=[CH2:36])[CH:29]=[CH:30][C:31]=1[Cl:32]>O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:25][C:26]1[CH:27]=[C:28]([NH:33][C:34](=[O:37])[CH:35]=[CH:36][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:29]=[CH:30][C:31]=1[Cl:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 28118Tetrafluoroboric acidHCID 2865472-(4-Methylpiperazin-1-yl)anilineHCID 13411358N-(3,4-Dichlorophenyl)prop-2-enamideHCID 23668193Sodium Nitrite

Product 1

HCID 70046281N-(3,4-Dichlorophenyl)-3-[2-(4-methylpiperazin-1-yl)phenyl]-acrylamide

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 887MethanolSolvent
HCID 962WaterSolvent2×

Procedure

In a flame-dried 3-neck round bottom flask containing a magnetic stir bar, water condensor and dry nitrogen (N2) inlet were placed 2-(4-methylpiperazin-1-yl)-aniline (0.200 g, 1.05 mmol) and 50% aqueous tetrafluoroboric acid (HBF4)(0.33 ml, 2.63 mmol). To the stirred mixture, sodium nitrite (0.076 g, 1.10 mmol) in 2 mL of water was added and stirring was continued at 0° C. for 30 minutes. A solution of N-(3,4-dichlorophenyl)-acrylamide (0.454 g, 2.1 mmol) in 4 mL of methanol, followed by palladium (II) acetate (5 mg) were then added and the reaction was refluxed for 30 minutes. After allowing the reaction to cool, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was washed with saturated brine and dried with CaSO4, filtered and concentrated in vacuo to a crude dark solid. Chromatography on silica gel, eluting with 75% ethyl acetate:hexanes, 100% ethyl acetate and finally 0.5% methanol: ethyl acetate provided a yellow solid, 0.221 g which was recrystallized from ethyl acetate to give the title product, 0.120 g.

Workup

  1. additionIn a flame-dried 3-neck round bottom flask containing a magnetic stir bar
  2. additionwere then added
  3. temperaturethe reaction was refluxed for 30 minutes
  4. customthe reaction
  5. temperatureto cool
  6. customthe solvent was removed in vacuo
  7. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried with CaSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to a crude dark solid
  12. washChromatography on silica gel, eluting with 75% ethyl acetate
  13. customhexanes, 100% ethyl acetate and finally 0.5% methanol: ethyl acetate provided a yellow solid, 0.221 g which
  14. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7fd6f1dda96b407eb7dd517a8a385a49
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06258953B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes