Hydrochloric Acid → t-Butyl 3-[N-[2-(1-adamantyl)ethyl]amino]propionate hydrochloride

HRID 2075873

Reaction equation

HRID 2075873 reaction equation
[ClH:1].[C:2]12([CH2:12][CH2:13][NH2:14])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.C(N(CC)CC)C.[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24].Cl.C(OCC)(=O)C>C(O)C>[ClH:1].[C:2]12([CH2:12][CH2:13][NH:14][CH2:24][CH2:23][C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 15458tert-Butyl acrylateHCID 27711382-(Adamantan-1-yl)ethan-1-amine hydrochloride

Product 1

HCID 21974130t-Butyl 3-[N-[2-(1-adamantyl)ethyl]amino]propionate hydrochlorideYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1-Adamantyl)ethylamine hydrochloride (1.0 g, 4.6 mmol) was dissolved in ethanol (10 ml), and triethylamine (0.65 ml, 4.6 mmol) and t-butyl acrylate (0.75 ml, 5.1 mmol) were added to the solution under ice-cooling. Then, the temperature was raised to room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, a 1 N aqueous sodium hydroxide solution (30 ml) and ethyl acetate (50 ml) were added to the residue, and layers were separated. The ethyl acetate layer was washed with water (50 ml) and a saturated aqueous sodium chloride solution (50 ml) successively and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography. The resulting oily matter (0.50 g, 1.6 mmol) was dissolved in diethyl ether (20 ml), and a 4 N solution of hydrogen chloride in ethyl acetate (1.0 ml, 4.0 mmol) was added thereto to precipitate a solid. This solid was filtered off with diethyl ether to give 0.33 g (23%) of the titled compound.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona 1 N aqueous sodium hydroxide solution (30 ml) and ethyl acetate (50 ml) were added to the residue, and layers
  4. customwere separated
  5. washThe ethyl acetate layer was washed with water (50 ml)
  6. dry with materiala saturated aqueous sodium chloride solution (50 ml) successively and dried over anhydrous magnesium sulfate
  7. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  8. customthe concentrate was purified by silica gel column chromatography
  9. dissolutionThe resulting oily matter (0.50 g, 1.6 mmol) was dissolved in diethyl ether (20 ml)
  10. customto precipitate a solid
  11. filtrationThis solid was filtered off with diethyl ether

Sources & evidence

ORD record
ord-0a22291b3d92417b8177618ccccda9c8
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Linked notes

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