Cesium carbonate → 1-(3-Phenylsulfonylphenyl)-4-tert-butyloxycarbonylpiperazine

HRID 855513Notes

Reaction equation

HRID 855513 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:53]1([S:59]([C:62]2[CH:63]=[C:64](Br)[CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[C:69]([O:73][C:74]([N:76]1[CH2:81][CH2:80][NH:79][CH2:78][CH2:77]1)=[O:75])([CH3:72])([CH3:71])[CH3:70]>O1CCOCC1>[C:53]1([S:59]([C:62]2[CH:63]=[C:64]([N:79]3[CH2:78][CH2:77][N:76]([C:74]([O:73][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:75])[CH2:81][CH2:80]3)[CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 640920Benzene, 1-bromo-3-(phenylsulfonyl)-

Product 1

HCID 688047411-(3-Phenylsulfonylphenyl)-4-tert-butyloxycarbonylpiperazineYield 71.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (62 mg, 0.1 mmol) and cesium carbonate (329 mg, 1.01 mmol) in dry dioxane (2 ml) were sonicated for 45 min, under argon. To this solution was added 3-phenylsulfonylbromobenzene (D2) (200 mg, 0.67 mmol) and 1-(tert-butyloxycarbonyl)piperazine (314 mg, 1.68 mmol) and the reaction heated at 100° C. for 18 h. The reaction mixture was evaporated in vacuo and the residue partitioned between water (50 ml) and dichloromethane (50 ml). The organic layer was washed with sat. sodium hydrogen carbonate (50 ml), 10% citric acid (50 ml), brine (50 ml) and then dried (MgSO4). Solvents evaporated in vacuo and the residue purified by column chromatography (silica gel; 0-60% ethyl acetate/petroleum ether) to give the product as a colourless oil (192 mg, 71%)

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue partitioned between water (50 ml) and dichloromethane (50 ml)
  3. washThe organic layer was washed with sat. sodium hydrogen carbonate (50 ml), 10% citric acid (50 ml), brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customSolvents evaporated in vacuo
  6. customthe residue purified by column chromatography (silica gel; 0-60% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-ddeb902ce7a64ae688d3c01c150e46fa
Source dataset
uspto-grants-2007_08
Patent number
US07262188B2

Reaction notes

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