Methyl Isobutyl Ketone → HCID 20382323, Verbindung

HRID 1973843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1973843
C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C.[CH3:14][O:15][CH2:16][C:17]1([N:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24](=[O:27])[CH2:25][CH3:26])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[C:34]1([CH2:44][CH2:45]OS(C2C=CC(C)=CC=2)(=O)=O)[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1>O>[CH3:14][O:15][CH2:16][C:17]1([N:23]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:24](=[O:27])[CH2:25][CH3:26])[CH2:22][CH2:21][N:20]([CH2:45][CH2:44][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][CH:35]=2)[CH2:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 162172NoralfentanilHCID 2704832-(naphthalen-1-yl)ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 20382323HCID 20382323, VerbindungAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6.4 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone is stirred and refluxed with water-separator. Then there are added 4.1 parts of N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide and 5.5 parts of [2-(1-naphthalenyl)ethyl]4-methylbenzenesulfonate and the whole is stirred and refluxed for 20 hours. The reaction mixture is cooled to room temperature and poured onto water. The organic phase is separated, washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 7% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue solidifies on triturating in hexane. The product is filtered off and crystallized from a small amount of 2,2'-oxybispropane, yielding 2.8 parts (43.4%) of N-{4-(methoxymethyl)-1-[2-(1-naphthalenyl)ethyl]-4-piperidinyl}-N-phenylpropanamide; mp. 109.8° C.

Aufarbeitung

  1. stirringthe whole is stirred
  2. temperaturerefluxed for 20 hours
  3. additionpoured onto water
  4. customThe organic phase is separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and 7% of methanol as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customon triturating in hexane
  14. filtrationThe product is filtered off
  15. customcrystallized from a small amount of 2,2'-oxybispropane

Quellen und Nachweise

ORD-Eintrag
ord-470cf4ab0c7a47028a02c409f6ded532
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03998834

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