Hydrochloric Acid → 3,5-Di-tert-butyl-2-[(methylamino)methyl]phenol

HRID 733303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733303
Cl.[NH2:2][CH2:3][C:4]1[C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:8][C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][C:5]=1[OH:18].[CH2:19]1N2CN3CN(C2)CN1C3.O.Cl>C(O)(=O)C.O>[C:10]([C:9]1[C:4]([CH2:3][NH:2][CH3:19])=[C:5]([OH:18])[CH:6]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=1)([CH3:11])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4101HexamethylenetetramineHCID 452597712-(Aminomethyl)-3,5-di-tert-butylphenol hydrochloride

Produkt 1

HCID 101061223,5-Di-tert-butyl-2-[(methylamino)methyl]phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 1.25 g (4.60 mmol) of the product of Example 19 (as the hydrochloride salt) in 10 mL of acetic acid-water (11:3) was added 0.75 g (5.35 mmol) of hexamethylenetetramine. The mixture was refluxed for 3 h then treated with 6 mL of water and 3 mL of conc. hydrochloric acid. Heating was continued for 10 min at which point the reaction mixture was cooled and concentrated in vacuo to remove the acetic acid. The residue was partitioned between EtOAc and water, and the aqueous layer was separated and extracted. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The product was purified on a silica gel flash chromatography column eluted with 5% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. temperatureHeating
  3. temperaturewas cooled
  4. concentrationconcentrated in vacuo
  5. customto remove the acetic acid
  6. customThe residue was partitioned between EtOAc and water
  7. customthe aqueous layer was separated
  8. extractionextracted
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated
  13. customThe product was purified on a silica gel flash chromatography column
  14. washeluted with 5% EtOAc-hexane
  15. customEvaporation of the purified fractions
  16. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f4c3ad6ccc1f49cfa49c4ec584de9eb7
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589127B2

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