Sodium Chloride → 3-Pyridin-3-ylcyclohexanamine

HRID 571966Notes

Reaction equation

HRID 571966 reaction equation
Cl.[NH2:2]O.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]2)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[Na+].[Cl-]>CO.O.C1COCC1>[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH2:2])[CH2:11]2)[CH:5]=1

Participants

10

Reactant 6

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 21226445Aluminium lithium hydrideHCID 221008783-(Pyridin-3-yl)cyclohexanone

Product 1

HCID 594861283-Pyridin-3-ylcyclohexanamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Hydroxylamine hydrochloride (67.7 mg, 0.975 mmol) was added to a stirred mixture of 8c (122 mg, 0.696 mmol) and potassium carbonate (96.0 mg, 0.696 mmol) in MeOH (3.00 mL) and water (600 μl). After the reaction was deemed to be complete, the reaction mixture was partially concentrated in vacuo and partitioned between EtOAc and brine. The layers were separated, and the aq. layer was extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford a crude residue (m/z (ES) 191 (MH)+), which was dissolved in THF (3.50 mL) and cooled to 0° C. Lithium aluminum hydride (106 mg, 2.78 mmol) was added in several portions, and after the reaction was deemed to be complete, 1N NaOH was added. The resulting mixture was saturated with NaCl(s) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound, 8d. m/z (ES) 177 (MH)+

Workup

  1. concentrationthe reaction mixture was partially concentrated in vacuo
  2. custompartitioned between EtOAc and brine
  3. customThe layers were separated
  4. extractionthe aq. layer was extracted with EtOAc
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a crude residue (m/z (ES) 191 (MH)+), which
  9. extractionextracted with EtOAc
  10. dry with materialThe combined organics were dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0259734d63c1445db1a13681ed9b5225
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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