Sodium Thiosulfate → HCID 58382244, compound

HRID 1628048Notes

Reaction equation

HRID 1628048 reaction equation
[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:18].[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH2:22][CH2:21]1.FC(F)(F)S(O)(=O)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[I:18][C:29]1[CH:30]=[CH:31][C:26]([N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)=[C:27]([CH3:32])[CH:28]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 62406Trifluoromethanesulfonic acidHCID 2319521-methyl-4-(2-methylphenyl)piperazineHCID 10883201Bis(pyridine)iodonium tetrafluoroborate

Product 1

HCID 58382244HCID 58382244, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of bis(pyridine)iodonium tetrafluoroborate (2.15 g, 5.78 mmol) and DCM (50 mL) at rt was added 1-methyl-4-o-tolylpiperazine (1.00 g, 5.26 mmol). A solution of trifluoromethanesulfonic acid (1 mL, 11 mmol) in DCM (25 mL) was added over about 3 min at rt. The mixture was then treated with saturated aqueous Na2S2O3 (30 mL), extracted with DCM (2×50 mL), washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/petroleum ether: 20%-100%) to give 1-(4-iodo-2-methylphenyl)-4-methylpiperazine, (0.40 g, 24%).

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/petroleum ether: 20%-100%)

Sources & evidence

ORD record
ord-659f1e3b75e34c09adc7ed3702412b6e
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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