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Thiophene → HCID 13094234, Verbindung

HRID 1164365
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1164365
S1C=CC=C1.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:20]#[N:21])[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)=[C:9]([CH3:22])[CH:8]=1.Cl.[C:24]1([C:30]2([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+].[H][H]>[Pd].C(O)C>[C:20]([C:13]1([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][C:9]=2[CH3:22])[CH2:18][CH2:17][CH:16]([N:33]2[CH2:32][CH2:31][C:30]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:35][CH2:34]2)[CH2:15][CH2:14]1)#[N:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 8030ThiopheneHCID 517045Sodium AcetateHCID 205117981-(4-Fluoro-2-methylphenyl)-4-oxocyclohexanecarbonitrileHCID 53444519Ethyl 4-phenylpiperidine-4-carboxylate--hydrogen chloride (1/1)HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 13094234
HCID 13094234, Verbindung
Ausbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol are added 4.7 parts of 1-(4-fluoro-2-methylphenyl)-4-oxocyclohexanecarbonitrile, 5.4 parts of ethyl 4-phenyl-4-piperidinecarboxylate hydrochloride, 2 parts of sodium acetate and 120 parts of ethanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charocal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off over Hyflo and the filtrate is evaporated. From the residue, the free base is liberated in the conventional manner with ammonium hydroxide and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and ethanol (98.5:1.5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from ethanol, yielding 3 parts (33.4%) of ethyl 1-[4-cyano-4-(4-fluoro-2-methylphenyl)cyclohexyl]-4 -phenyl-4-piperidinecarboxylate; mp. 135.2° C.

Aufarbeitung

  1. filtrationthe catalyst is filtered off over Hyflo
  2. customthe filtrate is evaporated
  3. extractionthe product is extracted with dichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and ethanol (98.5:1.5 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b99139ca3569457cb1096477051642aa
Quelldatensatz
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04369184

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