Hydrochloric Acid → 7-(5-Ethoxypyridin-3-yl)-1,7-diazaspiro[4.4]nonane

HRID 967929Notes

Reaction equation

HRID 967929 reaction equation
C([N:8]1[C:12]2([CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([O:23][CH2:24][CH3:25])[CH:22]=3)[CH2:13]2)[CH2:11][CH2:10][CH2:9]1)C1C=CC=CC=1.Cl.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:24]([O:23][C:21]1[CH:22]=[C:17]([N:14]2[CH2:15][CH2:16][C:12]3([NH:8][CH2:9][CH2:10][CH2:11]3)[CH2:13]2)[CH:18]=[N:19][CH:20]=1)[CH3:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 222912451-Benzyl-7-(5-ethoxypyridin-3-yl)-1,7-diazaspiro[4.4]nonaneHCID 178418361HCID 178418361, compound

Product 1

HCID 222912427-(5-Ethoxypyridin-3-yl)-1,7-diazaspiro[4.4]nonaneYield 91.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-benzyl-7-(5-ethoxy-3-pyridyl)-1,7-diazaspiro[4.4]nonane (540 mg, 1.6 mmol) in ethanol (25 mL) in a pressure bottle was added concentrated HCl (1 mL) and Pearlman's catalyst (Pd(OH)2, 20% on carbon, 50 mg). The solution was shaken under 50 psi of hydrogen gas for 8 h. The catalyst was removed by filtration through Celite, and the filter cake was washed with ethanol (20 mL). The solvent was removed by rotary evaporation, and the residue was basified with saturated aqueous sodium bicarbonate to pH 8-9. Solid sodium chloride (2 g) was added, and the mixture was extracted with chloroform (4×20 mL). The combined chloroform extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to afford 360.7 mg of the desired compound as a light brown viscous liquid (91.1%).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter cake was washed with ethanol (20 mL)
  3. customThe solvent was removed by rotary evaporation
  4. additionSolid sodium chloride (2 g) was added
  5. extractionthe mixture was extracted with chloroform (4×20 mL)
  6. dry with materialThe combined chloroform extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-9783016ef1764304974e59487ab87296
Source dataset
uspto-grants-2005_10
Patent number
US06956042B2

Reaction notes

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