Sodium Hydroxide → Ammonia

HRID 1779555Notes

Reaction equation

HRID 1779555 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCOCC1.[C:13]([N:17]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:23]/[CH:24]=[CH:25]/[CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33](=O)[CH2:34][CH3:35])[CH2:28]2)[CH2:18]1)(=O)[CH2:14][CH3:15].[OH-].[Na+]>O.O1CCCC1>[CH2:33]([N:29]1[CH2:30][CH2:31][CH2:32][N:27]([CH2:26]/[CH:25]=[CH:24]/[CH2:23][N:19]2[CH2:20][CH2:21][CH2:22][N:17]([CH2:13][CH2:14][CH3:15])[CH2:18]2)[CH2:28]1)[CH2:34][CH3:35].[NH3:17]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 19956381HCID 19956381, compoundHCID 21226445Aluminium lithium hydride

Product 2

HCID 222AmmoniaHCID 19956402HCID 19956402, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.68 g (17.9 mmol) of lithium aluminium hydride, 10 ml of dioxane and 1 g (2.97 mmol) of (E)-1,4-bis(3-propionylhexahydro-pyrimidin-1-yl)but-2-ene is stirred for 15 h at 100° C., with stirring and under a nitrogen atmosphere. After cooling to 5° C. in an ice-bath, there are added dropwise to the reaction mixture, in succession, a mixture of 0.53 ml of water and 2 ml of tetrahydrofuran, 0.53 ml of 1N sodium hydroxide solution and 1.1 ml of water, care being taken to ensure that the temperature does not exceed 15° C. The mixture is stirred for a further 1 h at room temperature and is filtered, the filtration residue is washed with tetrahydrofuran, and the filtrate is then concentrated by evaporation in vacuo. The oily residue is purified by means of flash chromatography over silica gel having a particle size of 0.04-0.063 mm, using methylene chloride-methanol (10:1) and methylene chloride-methanol-concentrated ammonia (100:10:0.5). Concentration of the product-containing fractions by evaporation yields the title compound in the form of an oil, Rf value=0.56 (silica gel/methylene chloride:methanol:concentrated ammonia (150:50:1)).

Workup

  1. stirringwith stirring and under a nitrogen atmosphere
  2. temperatureAfter cooling to 5° C. in an ice-bath
  3. additionthere are added dropwise to the reaction mixture, in succession
  4. customdoes not exceed 15° C
  5. stirringThe mixture is stirred for a further 1 h at room temperature
  6. filtrationis filtered
  7. washthe filtration residue is washed with tetrahydrofuran
  8. concentrationthe filtrate is then concentrated by evaporation in vacuo
  9. customThe oily residue is purified by means of flash chromatography over silica gel having a particle size of 0.04-0.063 mm
  10. customConcentration of the product-containing fractions by evaporation

Sources & evidence

ORD record
ord-82f3fb14d26a4f4980277dc605993064
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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