Water → 2-(4-(4-((2,4-Diaminophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972680Notes

Reaction equation

HRID 1972680 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([OH:37])([C:33]([F:36])([F:35])[F:34])[C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)(=[O:15])=[O:14])([O-])=O.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.O>CCO>[NH2:1][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([OH:37])([C:29]([F:32])([F:31])[F:30])[C:33]([F:34])([F:35])[F:36])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 493570RiboflavinHCID 866704322-(4-(4-((2,4-Dinitrophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

Product 1

HCID 866704332-(4-(4-((2,4-Diaminophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanolYield 87.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(4-(4-((2,4-dinitrophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (0.13 g, 0.22 mmol) in EtOH (5 mL) was added palladium, 10 wt % (dry basis) on activated carbon, wet, Degussa type E101 NE/W, water about 50% (26 mg, 0.24 mmol, Sigma-Aldrich, St. Louis, Mo.). The reaction vessel was carefully evacuated and backfilled with hydrogen. This was repeated twice and then the solution was left under an atmosphere of hydrogen (1 atm; 101.3 kpascal) for 18 h. The reaction vessel was then carefully evacuated and backfilled with N2. The solution was filtered through a syringe filter and the filtrate was concentrated onto silica. Purification by silica gel chromatography (0 to 6% MeOH/DCM) afforded 2-(4-(4-((2,4-diaminophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (96 mg) as an off-white solid.

Workup

  1. dry with materialpalladium, 10 wt % (dry basis) on activated carbon
  2. customThe reaction vessel was carefully evacuated
  3. customThe reaction vessel was then carefully evacuated
  4. filtrationThe solution was filtered through a syringe
  5. filtrationfilter
  6. concentrationthe filtrate was concentrated onto silica
  7. customPurification by silica gel chromatography (0 to 6% MeOH/DCM)

Sources & evidence

ORD record
ord-0ef72151149c4d66a6dcf1e69e94eeb9
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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