Ethyl Acetate → HCID 23081198, compound

HRID 856142Notes

Reaction equation

HRID 856142 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[F:20][C:21]([F:31])([F:30])[O:22][C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[F:20][C:21]([F:30])([F:31])[O:22][C:23]1[CH:28]=[CH:27][C:26]([N:1]2[CH2:6][CH2:5][CH:4]([N:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]3)[CH2:3][CH2:2]2)=[CH:25][CH:24]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 17750356tert-Butyl 4-(piperidin-4-yl)piperazine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 23081198HCID 23081198, compoundYield 42%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 4-piperidin-4-ylpiperazine-1-carboxylate (1.5 g, 5.67 mmol), 4-(trifluoromethoxy)bromobenzene (3.36 g, 13.92 mmol), palladium acetate (25 mg, 0.11 mmol), BINAP (87 mg, 0.14 mmol), and sodium tert-butoxide (1.07 g, 11.14 mmol) in toluene (20 ml) was stirred at 80° C. under a nitrogen atmosphere for 8 hours. The reaction mixture was allowed to return to room temperature, to which ethyl acetate (10 ml) and brine (20 ml) were added, and the mixture was filtered. The organic layer was separated, and dried over sodium sulfate. After filtration, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford tert-butyl 4-[1-(4-trifluoromethoxyphenyl)piperidin-4-yl]piperazine-1-carboxylate (1.01 g, 42%) as a yellow powder.

Workup

  1. additionwere added
  2. filtrationthe mixture was filtered
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-9cbccb13176d457ca05bdb4b20bd4e63
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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