Phenyl glycidyl ether → N-[4-[4-(2-hydroxy-3-phenoxypropyl)piperazin-1-yl]phenyl]methanesulfonamide

HRID 728829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728829
CS(O)(=O)=O.[N:6]1([C:12]2[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[O:23]1[CH:25]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24]1.C[O-].[Na+]>CO>[OH:23][CH:25]([CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:24][N:9]1[CH2:10][CH2:11][N:6]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:16][CH:17]=2)[CH2:7][CH2:8]1

Komponenten

5

Edukt 3

HCID 31217Phenyl glycidyl etherHCID 10942334Sodium MethoxideHCID 86745083N-[4-(piperazin-1-yl)phenyl]methanesulfonamide methanesulfonate

Produkt 1

HCID 14739896N-[4-[4-(2-hydroxy-3-phenoxypropyl)piperazin-1-yl]phenyl]methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Suspend a mixture of 20.0 g (56.9 mmol) of N-[4-(piperazin-1-yl)phenyl]methanesulfonamide methanesulfonate, 7.68 mL (56.9 mmol) of 1,2-epoxy-3-phenoxypropane and 3.07 g (56.9 mmol) of sodiummethoxide in 800 mL of 90% aqueous methanol and warm to 60° C. for 18 h. After 18 h, filter the precipitate and wash this precipitate with 100 mL of water and 100 mL of methanol. Suspend this solid precipitate in 500 mL of methanol and reflux for 1 h. After 1 h, cool the suspension to room temperature and filter to obtain the title compound.

Aufarbeitung

  1. filtrationfilter the precipitate
  2. washwash this precipitate with 100 mL of water and 100 mL of methanol
  3. temperaturereflux for 1 h
  4. waitAfter 1 h
  5. temperaturecool the suspension to room temperature
  6. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-e08eaf4769d64f228a4ae5d48c13dfb2
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051423

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