2-Fluoropyridine → HCID 18671377, compound

HRID 1057485Notes

Reaction equation

HRID 1057485 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][C:9]([CH3:14])([CH2:12][NH2:13])[CH2:10][NH2:11]>N1C=CC=CC=1>[NH2:11][CH2:10][C:9]([CH3:14])([CH3:8])[CH2:12][NH:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 97462-FluoropyridineHCID 817702,2-Dimethyl-1,3-propanediamine

Product 1

HCID 18671377HCID 18671377, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-fluoropyridine and 2,2-dimethyl-1,3-propanediamine (2 eq) in pyridine (0.3M) was refluxed for 18 hrs. and then concentrated by rotary evaporation. The solution was then concentrated in vacuo and the residue was partitioned between ethyl acetate and 10% sodium carbonate. The phases were separated, and the organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The product was purified by flash chromatography using 10:1:1 EtOH/NH4OH/H2O as eluent. EI-MS m/z 180 (M+H)+.

Workup

  1. temperaturewas refluxed for 18 hrs
  2. concentrationand then concentrated by rotary evaporation
  3. concentrationThe solution was then concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and 10% sodium carbonate
  5. customThe phases were separated
  6. washthe organic phase was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-c01c5c269bfa4c0bbf7f738d3225f2c5
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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