Hydrochloric Acid → HCID 45088871, compound

HRID 14280Notes

Reaction equation

HRID 14280 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]([CH3:12])[CH3:11])[CH:4]=1)#[N:2].Cl.[H][H]>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]([CH3:12])[CH3:11])[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 204987244-Cyano-2-(dimethylamino)methylpyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 45088871HCID 45088871, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-cyano-2-(dimethylamino)methylpyridine (800 mg, 4.97 mmol), palladium (80 mg, 10% Pd/C) and concentrated hydrochloric acid (3 mL) in methanol (30 mL) was shaken under 60 psi of hydrogen overnight. The reaction mixture was filtered through diatomaceous earth and the filter cake rinsed with water and methanol. The filtrate was concentrated under reduced pressure and the residue partitioned between water and methylene chloride. The aqueous layer was made alkaline with 1 N sodium hydroxide and extracted with methylene chloride. The organic layer was washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give an orange oil. Purification by flash column chromatography (97:3 2-propanol/ammonium hydroxide) gave 4-aminomethyl-2-(dimethylamino)methylpyridine 37 (492 mg): 1H NMR (500 Hz, CDCl3) δ 8.50 (d, J=5.1 Hz, 1H), 7.37 (s, 1H), 7.15 (d, J=5.1 Hz, 1H), 3.91 (s, 2H), 3.58 (s, 2H), 2.30 (s, 6H); ESI MS m/z 166 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake rinsed with water and methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue partitioned between water and methylene chloride
  5. extractionextracted with methylene chloride
  6. washThe organic layer was washed with saturated sodium chloride
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give an orange oil
  11. customPurification by flash column chromatography (97:3 2-propanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-29d7c1cd2dd449c9b6f5f96342b8ba1b
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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