Hydrochloric Acid → 4-(4-{2-Hydroxy-3-[(naphthalen-1-yl)oxy]propyl}piperazin-1-yl)-3-methoxyphenol

HRID 2247844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247844
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:16]1([O:26][CH2:27][CH:28]2[O:30][CH2:29]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(O)(C)C.Cl>CO.C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:29][CH:28]([OH:30])[CH2:27][O:26][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 14966308HCID 14966308, Verbindung

Produkt 1

HCID 1314914-(4-{2-Hydroxy-3-[(naphthalen-1-yl)oxy]propyl}piperazin-1-yl)-3-methoxyphenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 4.16 g. (0.02 mole) 1-(2-methoxy-4-hydroxyphenyl)-piperazine and 4.2 g. (0.021 mole) 2,3-epoxypropyl naphthyl ether in 50 ml. isopropanol is heated under reflux for 4 hours, while stirring. The solution is evaporated and the tarry residue obtained is dissolved in methanol. It is acidified with isopropanolic hydrochloric acid and diethyl ether carefully added thereto, an oily product precipitating out which is separated by decanting off. The solution is diluted with acetone. After a short time, the compound begins to crystallise out. When crystallisation is complete, the crystals are filtered off with suction and again recrystallised from methanol/diethyl either. Yield 4.8 g. (50% of theory); m.p. 230°-232° C.

Aufarbeitung

  1. temperatureunder reflux for 4 hours
  2. customThe solution is evaporated
  3. customthe tarry residue obtained
  4. additioncarefully added
  5. customan oily product precipitating out which
  6. customis separated
  7. customby decanting off
  8. additionThe solution is diluted with acetone
  9. customto crystallise out
  10. customWhen crystallisation
  11. filtrationthe crystals are filtered off with suction
  12. customagain recrystallised from methanol/diethyl either

Quellen und Nachweise

ORD-Eintrag
ord-82f7cfa5078c448494299f8eb40bc5d3
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05037828

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