Potassium Iodide → HCID 18377392, compound

HRID 2301135Notes

Reaction equation

HRID 2301135 reaction equation
[CH:1]1(O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.S(Cl)(Cl)=O.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(Cl)(Cl)Cl.C(C(C)=O)C.O>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 228191-IndanolHCID 24386Thionyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18377392HCID 18377392, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
0 °C

Procedure

1-Indanol (2.3 g, 17 mmol) was dissolved in chloroform (25 ml), and the solution was mixed with thionyl chloride (1.4 ml, 19 mmol) and stirred at 0° C. for 30 minutes and then at room temperature for 30 minutes. The solvent was removed by evaporation from the reaction solution under a reduced pressure, and the thus obtained residue was mixed with t-butoxycarbonylpiperazine (3.1 g, 17 mmol), potassium carbonate (6.0 g, 48 mmol) and potassium iodide (2.8 g, 17 mmol) and stirred overnight at 100° C. in methyl ethyl ketone (100 ml). The reaction solution was mixed with water, the reaction product was extracted with ethyl acetate, washed with water and saturated brine and dried with anhydrous sodium sulfate, the solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 3.6 g (12 mmol, 72%) of the title compound.

Workup

  1. waitat room temperature for 30 minutes
  2. customThe solvent was removed by evaporation from the reaction solution under a reduced pressure
  3. extractionthe reaction product was extracted with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under a reduced pressure
  7. customthe thus obtained material was separated
  8. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-69d16cffee99436e86c72af1ffee1205
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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