Sodium Iodide → HCID 14202062, compound

HRID 2297701Notes

Reaction equation

HRID 2297701 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15]OS(C)(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][NH:22][CH3:23].C1COCC1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:22]([CH3:23])[CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 11141145N-(benzyloxycarbonyl)-4-(mesyloxy)butylamineHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 14202062HCID 14202062, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine (2.51 g) in anhydrous dimethylformamide (28 ml) are added 2.0 M dimethylamine THF solution 12.5 ml. anhydrous potassium carbonate (1.72 g) and sodium iodide (3.74 g), and the mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 1.59 g (76%) of N-(benzyloxycarbonyl)-4-(dimethylamino)butylamine.

Workup

  1. extractionthe whole is extracted with ether
  2. washThe organic layer is washed with water and saturated brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c0e7d30ceb06427d9861a42c7a286e85
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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