Ethanamine, 2-fluoro-, hydrochloride → HCID 22911623, compound

HRID 1378426Notes

Reaction equation

HRID 1378426 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Cl.[F:12][CH2:13][CH2:14][NH2:15].C(N(C(C)C)CC)(C)C>C(O)C>[F:12][CH2:13][CH2:14][NH:15][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 783082-Chloro-5-nitropyridineHCID 81531Diisopropylethylamine

Product 1

HCID 22911623HCID 22911623, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2-chloro-5-nitropyridine (2.4 g, 0.015 mol), 2-fluoroethylamine hydrochloride (1.75 g, 0.0175 mol) and diisopropylethylamine (7.0 ml, 0.040 mol) in absolute ethanol (50 ml) was kept under nitrogen at ambient temperature (24° C.) for 22 hours, warmed slowly to the reflux temperature during 6 hours and refluxed for 18 hours. It was then concentrated in vacuo. The residue was mixed with saturated NaHCO3 and extracted with EtOAc. The extract was washed with water and brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with CH2 cl2. The product was crystallized from methyl tert butyl ether to give 1.25 g of the titled product, mp 126°-127° C.

Workup

  1. customwas kept under nitrogen at ambient temperature
  2. custom(24° C.)
  3. customfor 22 hours
  4. temperaturewarmed slowly to the reflux temperature during 6 hours
  5. temperaturerefluxed for 18 hours
  6. concentrationIt was then concentrated in vacuo
  7. additionThe residue was mixed with saturated NaHCO3
  8. extractionextracted with EtOAc
  9. washThe extract was washed with water and brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customThe residue was chromatographed on silica gel with CH2 cl2
  13. customThe product was crystallized from methyl tert butyl ether

Sources & evidence

ORD record
ord-61432901dfc141d7bbc17ba6a52f9dac
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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