Dimethylamine → 2-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one

HRID 465423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465423
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH:5]([OH:27])[CH2:6][NH:7][CH:8]([CH3:26])[CH2:9][C:10]1[CH:25]=[CH:24][C:13]([O:14][CH2:15][C:16]2[O:17][CH:18]=[C:19]([OH:23])[C:20](=[O:22])[CH:21]=2)=[CH:12][CH:11]=1.[CH3:31][NH:32][CH3:33].[CH2:34]=O>C(O)C.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH:5]([OH:27])[CH2:6][NH:7][CH:8]([CH3:26])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]2[O:17][C:18]([CH2:31][N:32]([CH3:34])[CH3:33])=[C:19]([OH:23])[C:20](=[O:22])[CH:21]=2)=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 198745272-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

Produkt 1

HCID 198745062-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A solution of 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one 0.8 g) in ethanol, was added to a mixture of dimethylamine (0.28 ml of a 33% solution, in ethanol) and formaldehyde (0.175 ml of a 37% aq. solution) in ethanol:water (95:5), (50 ml), at room temperature and allowed to stand for 1h. The solvent was evaporated in vacuo, the residue was partitioned between ethyl acetate and water separated and the organic extracts dried (magnesium sulphate), filtered and evaporated to an oil which was chromatographed on silica. Elution with chloroform: methanol (95:5) gave 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one (0.4 g) as a 49:51 mixture of diastereoisomers.

Aufarbeitung

  1. customat room temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. customseparated
  5. dry with materialthe organic extracts dried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated to an oil which
  8. customwas chromatographed on silica
  9. washElution with chloroform: methanol (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-99854ab73eda4a74a63280b14a8960e4
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153210

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