Ammonia → 4-Aminoadamantane-1-carboxamide

HRID 589652Notes

Reaction equation

HRID 589652 reaction equation
O=[C:2]1[CH:9]2[CH2:10][C:5]3([C:12]([NH2:14])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[NH3:15].[H][H]>CO.[Pd].O>[NH2:15][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([NH2:14])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2

Participants

7

Reactant 3

HCID 222AmmoniaHCID 28434324-Oxoadamantane-1-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 668634414-Aminoadamantane-1-carboxamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

26 g of 4-oxoadamantane-1-carboxamide (2) was put into a sealed container and 190 mL of 7N NH3 dissolved in MeOH was added thereto. Then, 1 g of a palladium catalyst (10 wt % Pd/C) was put into the reactor, and the reactor was filled with a nitrogen gas and the reactants were stirred for 18 hours. After the nitrogen gas was completely replaced with a hydrogen gas, the reactants were stirred for 24 hours and then filtered and distilled under a reduced pressure to provide a solid product. This solid product was placed and stirred in 100 mL of water and after the solids were removed therefrom, the remaining solution was distilled under a reduced pressure to provide 20 g of 4-aminoadamantane-1-carboxamide (3).

Workup

  1. additionwas added
  2. additionthe reactor was filled with a nitrogen gas
  3. stirringthe reactants were stirred for 24 hours
  4. filtrationfiltered
  5. distillationdistilled under a reduced pressure
  6. customto provide a solid product
  7. customafter the solids were removed
  8. distillationthe remaining solution was distilled under a reduced pressure

Sources & evidence

ORD record
ord-4efe59ca5e0d444f87b813e4d3825cc7
Source dataset
uspto-grants-2016_01
Patent number
US09233957B2

Reaction notes

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