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

HRID 2116470Notes

Reaction equation

HRID 2116470 reaction equation
C1(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:40]1([S:46]([C:49]2[CH:50]=[C:51](Br)[CH:52]=[CH:53][CH:54]=2)(=[O:48])=[O:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[C:56]([O:60][C:61]([N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1)=[O:62])([CH3:59])([CH3:58])[CH3:57]>O1CCOCC1>[C:40]1([S:46]([C:49]2[CH:50]=[C:51]([N:66]3[CH2:65][CH2:64][N:63]([C:61]([O:60][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:62])[CH2:68][CH2:67]3)[CH:52]=[CH:53][CH:54]=2)(=[O:48])=[O:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 640920Benzene, 1-bromo-3-(phenylsulfonyl)-HCID 10993848Diphenylphosphino-1,1'-binaphthyl

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 dichbromethane (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 dichbromethane (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-f0f83f9a180e4664b3991bd7a836af72
Source dataset
uspto-grants-2008_10
Patent number
US07439245B2

Reaction notes

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