1-Chloro-3-phenoxy-2-propanol → 7-[3-(3-Phenoxy-2-hydroxypropylamino)-propyl]-theophylline

HRID 614326

Reaktionsgleichung

Reaktionsgleichung von HRID 614326
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:13](=[O:15])[N:11]([CH3:12])[C:10](=[O:16])[N:9]([CH3:17])[C:8]=2[N:7]=[CH:6]1.Cl[CH2:19][CH:20]([OH:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[O:22]([CH2:21][CH:20]([OH:29])[CH2:19][NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:13](=[O:15])[N:11]([CH3:12])[C:10](=[O:16])[N:9]([CH3:17])[C:8]=2[N:7]=[CH:6]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 943001-Chloro-3-phenoxy-2-propanolHCID 29652267-(3-aminopropyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Produkt 1

HCID 213292787-[3-(3-Phenoxy-2-hydroxypropylamino)-propyl]-theophylline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 75 g of 7-(3-aminopropyl)-theophylline and 27.4 g of 1-chloro-3-phenoxy-2-propanol is heated for 8 hours at 130° to 140° C. After the melt has been cooled to 70°-90° C., ethanol is added to it, followed by brief boiling under reflux. After standing overnight, the untreated and precipitated aminopropyl theophylline hydrochloride is filtered off under suction, the filtrate is acidified with alcoholic hydrochloric acid, heavily concentrated and acetone added until crystallisation begins. The reaction product then separates and is recrystallised from methanol. Yield 30.2 g. Melting point of the hydrochloride: 183°-186° C.

Aufarbeitung

  1. temperatureis heated for 8 hours at 130° to 140° C
  2. temperatureAfter the melt has been cooled to 70°-90° C.
  3. temperatureunder reflux
  4. customthe untreated and precipitated aminopropyl theophylline hydrochloride
  5. filtrationis filtered off under suction
  6. concentrationheavily concentrated
  7. additionacetone added until crystallisation
  8. customis recrystallised from methanol
  9. custom183°-186° C.

Quellen und Nachweise

ORD-Eintrag
ord-efeded0832d9465981883351326e06bc
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04144340

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