Potassium Iodide → HCID 18770440, compound

HRID 479389Notes

Reaction equation

HRID 479389 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][CH:27]([CH2:42]Br)[CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[OH-].[Na+]>CN(C)C=O>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][CH:27]([CH2:42][N:3]([CH3:4])[CH3:2])[CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18770378HCID 18770378, compound

Product 1

HCID 18770440HCID 18770440, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylamine hydrochloride (638 mg; 7.8 mmol), potassium carbonate (1.2 g; 8.7 mmol) and potassium iodide (144 mg; 0.87 mmol) were added to a solution in dimethylformamide (10 ml) of 1,3-bis(1-tert-butoxycarbonyl-4-piperidinyl)-2-(bromomethyl)propane (437 mg; 0.87 mmol) synthesized by the above process, and the mixture was stirred for 4 hours in a bath controlled at 60° C. A 0.1N aqueous solution of sodium hydroxide was added to the reaction mixture to conduct extraction with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 243 mg (yield: 60%) of the title compound as a colorless oil.

Workup

  1. customsynthesized by the above process
  2. customcontrolled at 60° C
  3. extractionextraction with diethyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f53b4b8d716948a4a2345e07068069a0
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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