Potassium Hydroxide → 1-(tert-Butoxycarbonyl)-4-[4-(pyridin-4-yl)benzenesulfonyl]piperazine

HRID 352825Notes

Reaction equation

HRID 352825 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(B(CC)[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)C.[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 3

HCID 14797Potassium HydroxideHCID 133188714-(Diethylboranyl)pyridineHCID 166655764-(4-BOC-piperazinosulfonyl)bromobenzene

Product 1

HCID 227099051-(tert-Butoxycarbonyl)-4-[4-(pyridin-4-yl)benzenesulfonyl]piperazine

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromobenzenesulfonyl)-4-(tert-butoxycarbonyl)piperazine (1.00 g) in tetrahydrofuran (50 ml) were added diethyl(pyridin-4-yl)boron (470 mg), tetrabutylammonium bromide (480 mg), potassium hydroxide (625 mg), tetrakistriphenylphosphine palladium (285 mg) and water (800 μl) at room temperature. The resulting mixture was heated under reflux for 1 hour. After allowed to cool down, the reaction mixture was added with ethyl acetate (50 ml) and water (100 ml). The water layer thus separated was extracted with ethyl acetate (50 ml). The organic layers were combined, washed with saturated aqueous NaCl solution (50 ml), dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:ethyl acetate=1:1), whereby the title compound (540 mg) was obtained as a colorless transparent viscous substance.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool down
  4. customThe water layer thus separated
  5. extractionwas extracted with ethyl acetate (50 ml)
  6. washwashed with saturated aqueous NaCl solution (50 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by chromatography on a silica gel column (methylene chloride:ethyl acetate=1:1), whereby the title compound (540 mg)
  11. customwas obtained as a colorless transparent viscous substance

Sources & evidence

ORD record
ord-7ba15cab61b14a178d7f70ce927254c3
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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