StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Water → HCID 178468978, Verbindung

HRID 351542
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 351542
[CH:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:14]([O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)=[O:18])[CH3:15].C([BH3-])#N.[Na+].O>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:1]1([C@@H:7]2[CH2:12][CH2:11][C@H:10]([N:28]3[CH2:27][CH2:26][N:25]([C:22]4[CH:21]=[CH:20][C:19]([C:17]([O:16][CH2:14][CH3:15])=[O:18])=[CH:24][CH:23]=4)[CH2:30][CH2:29]3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 41690(1,1'-Bicyclohexyl)-4-oneHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 178468978HCID 178468978, VerbindungAusbeute 20,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026
Titanium isopropoxide
Katalysator
HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-cyclohexylcyclohexanone (1.54 g), 1-(4-ethoxycarbonylphenyl)piperazine (2 g) and titanium(IV) isopropoxide (3.18 ml) was stirred at room temperature. After 1 hour, the IR spectrum of the mixture showed no ketone band, and the viscous solution was diluted with absolute ethanol (8.5 ml). Sodium cyanoborohydride (0.343 g) was added, and the solution was stirred for 3 hours. Water (3 ml) was added with stirring, and the resulting in organic precipitate was filtered and washed with ethanol. The filtrate was extracted with ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with (hexane/ethyl acetate)=(3/1). The fractions containing the less polar compound were collected and evaporated under reduced pressure to give ethyl 4-[4-(cis-4-cyclohexylcyclohexyl)piperazin-1-yl]benzoate (692 mg) as byproduct. The fractions containing the more polar compound were collected and evaporated under reduced pressure to give ethyl 4-[4-(trans-4-cyclohexylcyclohexyl)piperazin-1-yl]benzoate (587 mg).

Aufarbeitung

  1. stirringthe solution was stirred for 3 hours
  2. stirringwith stirring
  3. filtrationthe resulting in organic precipitate was filtered
  4. washwashed with ethanol
  5. extractionThe filtrate was extracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe magnesium sulfate was filtered off
  8. customfiltrate was evaporated under reduced pressure
  9. washeluted with (hexane/ethyl acetate)=(3/1)
  10. additionThe fractions containing the less polar compound
  11. customwere collected
  12. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9d9de2240edd40cca52a14699746cbfa
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06743776B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion