1-Benzylpiperazine → HCID 22142247, compound

HRID 2414486Notes

Reaction equation

HRID 2414486 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CC(C)([O-])C.[Na+].[CH2:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:20]([N:27]1[CH2:32][CH2:31][N:30]([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]3)[CH2:29][CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 759941-BenzylpiperazineHCID 7218471-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 22142247HCID 22142247, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

1-acetyl-5-bromoindoline (3.0 g, 12.5 mmol) was dissolved in toluene (60 mL). To this was added, sodium t-butoxide (1.68 g, 17.5 mmol), N-benzylpiperazine (2.4 mL, 13.8 mmol), S-BINAP (0.93 g, 1.5 mmol) and Pd2(dba)3 (0.46 g, 0.5 mmol). The mixture was degassed via three cycles of vacuum and nitrogen sparge and then stirred at 95° C. until GC analysis confirmed that the reaction was complete (1 h). The mixture was diluted with ethyl acetate (150 mL), washed with water and extracted with 2N HCl (2×100 mL). The combined aqueous extract was basified with concentrated ammonium hydroxide and extracted with ethyl acetate (2×100 mL). The combined organic extract was dried (MgSO4) and concentrated to yield a solid (2.7 g) which was purified by chromatography to yield a white solid (1.81 g, 43%). Mp=150.5-152.8° C.

Workup

  1. additionTo this was added
  2. customThe mixture was degassed via three cycles of vacuum and nitrogen
  3. customsparge
  4. custom(1 h)
  5. additionThe mixture was diluted with ethyl acetate (150 mL)
  6. washwashed with water
  7. extractionextracted with 2N HCl (2×100 mL)
  8. extractionThe combined aqueous extract
  9. extractionextracted with ethyl acetate (2×100 mL)
  10. extractionThe combined organic extract
  11. dry with materialwas dried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-7c7eb69a4a4b468c8c9f8d3250f8f406
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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