tert-Butyl piperazine-1-carboxylate → HCID 67094789, compound

HRID 1710600

Reaction equation

HRID 1710600 reaction equation
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:48]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=1[O:57][C:58]([F:61])([F:60])[F:59].[C:62]([O:66][C:67]([N:69]1[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]1)=[O:68])([CH3:65])([CH3:64])[CH3:63].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:62]([O:66][C:67]([N:69]1[CH2:74][CH2:73][N:72]([C:48]2[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=2[O:57][C:58]([F:61])([F:60])[F:59])[CH2:71][CH2:70]1)=[O:68])([CH3:65])([CH3:63])[CH3:64]

Participants

7

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 247216412-Bromo-4-nitro(trifluoromethoxy)benzene

Product 1

HCID 67094789HCID 67094789, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 0.048 g palladium(II)-acetate (0.214 mmol) and 0.133 g BINAP (0.214 mmol) in 7 mL toluene was heated to 60° C., stirred for 10 min. and the obtained suspension was added dropwise to a solution of 0.51 g 2-bromo-4-nitro-1-(trifluoromethoxy)benzene (1.783 mmol), 0.343 g tert.butyl-piperazine-1-carboxylate (1.842 mmol) and 0.232 g sodium tert-butoxide (2.414 mmol) in 8 mL of toluene. The thus obtained reaction mixture was treated at 130° C. for 1.5 h in a commercial microwave oven. The organic layer was washed with water, the aqueous phase was extracted with dichloromethane and the combined organic layers were extracted with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was further purified via silica gel chromatography using a ISCO Companion system (eluent cyclohexane-ethyl acetate 5-25%) to yield 0.413 g of product.

Workup

  1. customThe thus obtained reaction mixture
  2. additionwas treated at 130° C. for 1.5 h in a commercial microwave oven
  3. washThe organic layer was washed with water
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. extractionthe combined organic layers were extracted with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe crude product was further purified via silica gel chromatography

Sources & evidence

ORD record
ord-33e18adf3c554e2bb7578855c5491576
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Linked notes

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