Sodium Iodide → Carbamic acid, [2-(cyclohexylmethylamino)ethyl]-, 1,1-dimethylethyl ester

HRID 1581810Notes

Reaction equation

HRID 1581810 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:12][NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:13]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7514N-MethylcyclohexylamineHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 22722898Carbamic acid, [2-(cyclohexylmethylamino)ethyl]-, 1,1-dimethylethyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(t-butoxycarbonyl)-2-bromoethylamine (1.0 g) in anhydrous dimethylformamide (15 ml) are added N-methylcyclohexylamine (0.64 ml), anhydrous potassium carbonate (0.9 g) and sodium iodide (2.0 g), and the mixture is stirred at room temperature for three days. Water is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution, 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 0.82 g (72%) of N-(t-butoxycarbonyl)-N′-cyclohexyl-N′-methylethylenediamine as oily matter.

Workup

  1. extractionthe whole is extracted with ether
  2. washThe organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution, 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-685a394c721849cdba65bf1296958970
Source dataset
uspto-grants-2004_05
Patent number
US06730784B2

Reaction notes

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