Formic Acid → N-methyl-N-(2-morpholinoethyl)-1-[1-(4-chlorophenyl)cyclobutyl]-2-methoxyethylamine

HRID 1650972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650972
Cl.Cl.[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][NH:11][CH:12]([C:16]2([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:19][CH2:18][CH2:17]2)[CH2:13][O:14][CH3:15])[CH2:5][CH2:4]1.[CH:27](O)=O.C=O>C(OCC)(=O)C>[CH3:27][N:11]([CH:12]([C:16]1([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH2:17][CH2:18][CH2:19]1)[CH2:13][O:14][CH3:15])[CH2:10][CH2:9][N:6]1[CH2:5][CH2:4][O:3][CH2:8][CH2:7]1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 67945593N-(2-morpholinoethyl)-1-[1-(4-chlorophenyl)cyclobutyl]-2-methoxyethylamine dihydrochloride

Produkt 1

HCID 19823697N-methyl-N-(2-morpholinoethyl)-1-[1-(4-chlorophenyl)cyclobutyl]-2-methoxyethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the product of Example 208 in the form of its free base (2.0 g), 98% formic acid (8 ml) and 37-40% aqueous formaldehyde solution (25 ml) was stirred at room temperature for 2 hours. The mixture was then heated at 95°-100° C. for 18 hours, cooled, basified and extracted with ether. The extract was washed with water and dried. Dry hydrogen chloride gas was passed into the ethereal solution. Evaporation of the solvent gave a residue which was heated with ethyl acetate (20 ml) to give a white solid which was partitioned between ether and water. The aqueous phase was basified and then extracted with ether. The extract was dried and evaporated to give a residue which was distilled using a Buchi Kugelrohr apparatus (200° C./0.5 mm) to give N-methyl-N-(2-morpholinoethyl)-1-[1-(4-chlorophenyl)cyclobutyl]-2-methoxyethylamine.

Aufarbeitung

  1. temperatureThe mixture was then heated at 95°-100° C. for 18 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. washThe extract was washed with water
  5. customdried
  6. customEvaporation of the solvent
  7. customgave a residue which
  8. customto give a white solid which
  9. customwas partitioned between ether and water
  10. extractionextracted with ether
  11. customThe extract was dried
  12. customevaporated
  13. customto give a residue which
  14. distillationwas distilled
  15. customa Buchi Kugelrohr apparatus (200° C./0.5 mm)

Quellen und Nachweise

ORD-Eintrag
ord-817a9a2e6f6042468242cd012e72aaa1
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925879

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