Dimethylamine → HCID 14202062, compound

HRID 1581811Notes

Reaction equation

HRID 1581811 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].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 674DimethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 11141145N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine

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 dimethylamine (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-76b025857015435db2a886aa204f7488
Source dataset
uspto-grants-2004_05
Patent number
US06730784B2

Reaction notes

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