Ethylene Glycol → 1-Acetyl-4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]piperidine

HRID 1656917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656917
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:19](O)[CH2:20][OH:21].CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[O:21][CH2:20][CH2:19][O:18]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidine

Produkt 1

HCID 191009161-Acetyl-4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]piperidineAusbeute 56,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 74.7 parts of 1-acetyl-4-(4-fluorobenzoyl)piperidine, 46.5 parts of 1,2-ethanediol, 3 parts of 4-methylbenzenesulfonic acid and 810 parts of benzene was stirred for 108 hours at reflux temperature using a water separator. After cooling, the reaction mixture was washed successively with 250 parts of water, 22.5 parts of ammonium hydroxide and 250 parts of water. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3COCH3 50:50). The eluent of the desired fraction was evaporated, yielding 50 parts (56.8%) of 1-acetyl-4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]piperidine (interm. 45).

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed successively with 250 parts of water, 22.5 parts of ammonium hydroxide and 250 parts of water
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3COCH3 50:50)
  8. customThe eluent of the desired fraction was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-95ea220e3ac344f188273d63989a108f
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256659

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