Hydrochloric Acid → 1-[2-(1-Adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]hexahydro-2,4-pyrimidinedione hydrochloride

HRID 2075902Notes

Reaction equation

HRID 2075902 reaction equation
[ClH:1].[C:2]12([CH2:12][CH2:13][N:14]([CH2:27][CH2:28][C:29]([O:31]C(C)(C)C)=O)[C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[O:16])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.C(OCC)(=O)C>O1CCOCC1>[ClH:1].[C:2]12([CH2:12][CH2:13][N:14]3[CH2:27][CH2:28][C:29](=[O:31])[N:17]([CH2:18][CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[C:15]3=[O:16])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 21974212HCID 21974212, compound

Product 1

HCID 219741151-[2-(1-Adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]hexahydro-2,4-pyrimidinedione hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 4 N solution of hydrogen chloride in 1,4-dioxane (2.5 ml) was added to 1-[2-(1-adamantyl)ethyl]-1-[2-(t-butoxycarbonyl)ethyl]-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-69) (0.23 g, 0.49 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, a 1 N aqueous sodium hydroxide solution (20 ml) and ethyl acetate (30 ml) were added to the residue, and layers were separated. The ethyl acetate layer was washed with water (20 ml) and a saturated aqueous sodium chloride solution (20 ml) successively and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the resulting oily matter was dissolved in diethyl ether (20 ml). A 4 N solution of hydrogen chloride in ethyl acetate (0.50 ml, 2.00 mol) was added thereto under ice-cooling, the mixture was concentrated under reduced pressure, and the precipitated solid was filtered off with ethyl acetate to give 0.17 g (79%) of the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 1 N aqueous sodium hydroxide solution (20 ml) and ethyl acetate (30 ml) were added to the residue, and layers
  3. customwere separated
  4. washThe ethyl acetate layer was washed with water (20 ml)
  5. dry with materiala saturated aqueous sodium chloride solution (20 ml) successively and dried over anhydrous magnesium sulfate
  6. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  7. dissolutionthe resulting oily matter was dissolved in diethyl ether (20 ml)
  8. temperatureunder ice-cooling
  9. concentrationthe mixture was concentrated under reduced pressure
  10. filtrationthe precipitated solid was filtered off with ethyl acetate

Sources & evidence

ORD record
ord-90bc4e796bee4f6682cb751a1370b519
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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