1,4-Dioxane → HCID 21281918, Verbindung

HRID 414243

Reaktionsgleichung

Reaktionsgleichung von HRID 414243
Cl.C[NH:3][C:4]([CH3:9])([C:6](O)=[O:7])[CH3:5].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:39])OC4C=CC=CC=4)=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(=O)([O-])O.[Na+].O1CCOCC1>CN(C)C1C=CN=CC=1.O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:25]=[CH:26][C:27]([N:30]4[C:6](=[O:7])[C:4]([CH3:9])([CH3:5])[NH:3][C:31]4=[O:39])=[CH:28][CH:29]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 981607Phenyl N-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamateHCID 567771322-Methyl-2-(methylamino)propanoic acid hydrochloride

Produkt 1

HCID 21281918HCID 21281918, VerbindungAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 23 parts of methyl 2-methylalanine hydrochloride, 55 parts of phenyl [4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]carbamate. 12.45 parts of sodium hydrogen carbonate, 10 parts of N,N-dimethyl-4-pyridinamine and 300 parts of 1,4-dioxane was stirred overnight at reflux temperature. Water was added till saturation. After stirring for another hour at reflux temperature, the mixture was cooled to room temperature. The product was filtered off, washed with water and 2,2'-oxybispropane and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 4-methyl-2-pentanone. The product was filtered off and dried. yielding 45.33 parts (84.4%) of 3-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-2,4-imidazolidinedione; mp. 255.0° C. (intermediate 19).

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureat reflux temperature
  3. filtrationThe product was filtered off
  4. washwashed with water and 2,2'-oxybispropane
  5. custompurified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 4-methyl-2-pentanone
  10. filtrationThe product was filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f33d77786e5d45618d70354830331f58
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791111

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