Piperazine → HCID 21071160, compound

HRID 1371979Notes

Reaction equation

HRID 1371979 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CC(C)([O-])C.[Na+].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.Br[C:60]1[CH:65]=[CH:64][C:63]([Cl:66])=[CH:62][C:61]=1[C:67]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:68]>C1(C)C=CC=CC=1>[Cl:66][C:63]1[CH:64]=[CH:65][C:60]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[C:61]([C:67]([C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)=[O:68])[CH:62]=1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 278924(2-bromo-5-chlorophenyl)(phenyl)methanoneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 21071160HCID 21071160, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

Piperazine (3.6 g, 42.5 mmol), Pd(II)acetate (0.007 g, 0.043 mmol), sodium t-butoxide (0.22 g, 2.4 mmol) and BINAP (0.042 g, 0.068 mmol) were stirred at room temperature in 10 mL dry toluene for 15 min. (2-Bromo-5-chloro-phenyl)-phenyl-methanone (0.5 g, 1.7 mmol) in 10 mL dry toluene was then added into the reaction mixture. The reaction mixture was refluxed at 110° C. for 20 hrs, filtered through a celite bed, washed with toluene, concentrated, taken in ethyl acetate and extracted with 1.5 (N) HCl solution three times. The combined aqueous layers were washed with diethyl ether. The aqueous layer was neutralized with 10% aqueous sodium hydroxide solution and then extracted with ethyl acetate three times. The combined ethyl acetate layers were washed with water and saturated brine solution, dried over anhydrous sodium sulfate and concentrated. Purification by flash chromatography (eluted with CHCl3-MeOH) afforded the title compound as product.

Workup

  1. additionwas then added into the reaction mixture
  2. filtrationfiltered through a celite bed
  3. washwashed with toluene
  4. concentrationconcentrated
  5. extractionextracted with 1.5 (N) HCl solution three times
  6. washThe combined aqueous layers were washed with diethyl ether
  7. extractionextracted with ethyl acetate three times
  8. washThe combined ethyl acetate layers were washed with water and saturated brine solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customPurification
  12. washby flash chromatography (eluted with CHCl3-MeOH)

Sources & evidence

ORD record
ord-96e2ed4a8069472ab8efe0fb027d7265
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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