Potassium Iodide → HCID 66598394, compound

HRID 1038530Notes

Reaction equation

HRID 1038530 reaction equation
N[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:41].[K+]>C(#N)C.O>[I:41][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 521998p-Toluenesulfonic acid monohydrateHCID 18526396tert-Butyl 4-[2-amino-4-(methoxycarbonyl)-phenyl]piperazine-1-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 66598394HCID 66598394, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 4-[2-amino-4-(methoxycarbonyl)phenyl]piperazine-1-carboxylate (231 mg, 0.657 mmol) in acetonitrile (6.6 mL), para-toluenesulfonic acid monohydrate (375 mg, 1.97 mmol) was added under ice-cold conditions, and then added a mixed solution of sodium nitrite (91 mg, 1.31 mmol) and potassium iodide (273 mg, 1.64 mmol) under ice-cold conditions, and the mixture was stirred at room temperature overnight. The reaction solution was added water and an aqueous solution of sodium thiosulfate under ice-cold conditions, and extracted with ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (127 mg (yield 43%)) was obtained as a white crystal.

Workup

  1. extractionan aqueous solution of sodium thiosulfate under ice-cold conditions, and extracted with ethyl acetate
  2. washThen, the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-bcf48d78cef349cdb1133bc760f03adb
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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