Methylamine → HCID 45091395, compound

HRID 1725345Notes

Reaction equation

HRID 1725345 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][CH2:6][CH2:7]OS(C)(=O)=O.[CH3:17][NH2:18]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][CH2:6][CH2:7][NH:18][CH3:17]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86605221HCID 86605221, compound

Product 1

HCID 45091395HCID 45091395, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methanesulfonic acid 2-(3,5-difluoro-phenoxy)-ethyl ester (1.2 g, 4.76 mmol), THF (30 ml) and 40% aqueous monomethylamine (30 ml) was heated under reflux for 8 hours. The reaction mixture was poured on water and extracted 3 times with diethyl ether (3×20 ml). The orghanic phase was washed with water, dried over magnesium sulfate and concentrated to dryness. The residue was chromatographed on silicagel eluting with methylene chloride-methanol (9-1) to give [2-(3,5-difluoro-phenoxy)-ethyl]-methyl-amine (0.63 g, 71%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. additionThe reaction mixture was poured on water
  4. extractionextracted 3 times with diethyl ether (3×20 ml)
  5. washThe orghanic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue was chromatographed on silicagel
  9. washeluting with methylene chloride-methanol (9-1)

Sources & evidence

ORD record
ord-4a3d3e662e7549189b2833200cc6b49b
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

Loading…