Ethanolamine → HCID 22723091, compound

HRID 2297704Notes

Reaction equation

HRID 2297704 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[NH2:9][CH2:10][CH2:11][OH:12].[CH:13]1([CH2:19][CH2:20]Br)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl-:22].[NH4+]>C(O)C>[ClH:22].[CH:13]1([CH2:19][CH2:20][NH:9][CH2:10][CH2:11][OH:12])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 700EthanolamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15440(2-Bromoethyl)cyclohexaneHCID 25517Ammonium Chloride

Product 1

HCID 22723091HCID 22723091, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous potassium carbonate (3.5 g) and sodium iodide (9.4 g) are added to a solution of 2-aminoethanol (1.9 ml) and 2-cyclohexylethyl bromide (4.0 g) in ethanol (42 ml), and the mixture is refluxed for 17 hours with stirring. A saturated aqueous ammonium chloride solution is added to the reaction mixture, and the mixture is washed with ether. A 4 N aqueous sodium hydroxide solution is added to the aqueous layer, and the whole is extracted with chloroform. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is dissolved in ethyl acetate. To the solution are added a 4 N solution of hydrogen chloride in ethyl acetate (4 ml) and then ether (10 ml) under ice cooling, and the resulting precipitate is filtered off to give 2.2 g (51%) of the titled compound (Reference compound No. 13-1) as crystals.

Workup

  1. temperaturethe mixture is refluxed for 17 hours
  2. washthe mixture is washed with ether
  3. additionA 4 N aqueous sodium hydroxide solution is added to the aqueous layer
  4. extractionthe whole is extracted with chloroform
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe resulting residue is dissolved in ethyl acetate
  9. additionTo the solution are added a 4 N solution of hydrogen chloride in ethyl acetate (4 ml)
  10. filtrationether (10 ml) under ice cooling, and the resulting precipitate is filtered off

Sources & evidence

ORD record
ord-e239c4ceae694970b7b1c853e989e360
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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