Hydrochloric Acid → 7-(5-Phenoxy-3-pyridyl)-1,7-diazaspiro[4,4]nonane

HRID 2076409Notes

Reaction equation

HRID 2076409 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][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[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]>[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)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 222912051-Benzyl-7-(5-phenoxypyridin-3-yl)-1,7-diazaspiro[4.4]nonaneHCID 178418361HCID 178418361, compound

Product 1

HCID 115438947-(5-Phenoxy-3-pyridyl)-1,7-diazaspiro[4,4]nonaneYield 92.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-benzyl-7-(5-phenoxy-3-pyridyl)-1,7-diazaspiro[4.4]nonane (690 mg, 1.79 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 catalysts 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 solution was extracted with chloroform (4×20 mL). The combined chloroform extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to afford 490 mg of the desired compound as a light brown viscous liquid (92.7%).

Workup

  1. customThe catalysts 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 solution 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-1d914b1d2df944c9ab023452b2cd9b59
Source dataset
uspto-grants-2011_04
Patent number
US07923559B2

Reaction notes

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