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3-Acetylbenzonitrile → HCID 10521779, Verbindung

HRID 865936
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 865936
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[CH3:3].[C:17]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24])(=O)[CH3:18].[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[CH3:3][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([CH:17]([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[C:23]#[N:24])[CH3:18])[CH2:15][CH2:16]1)[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 802223-AcetylbenzonitrileHCID 4311764Sodium borohydrideHCID 109440161-[2-(Propan-2-yloxy)phenyl]piperazine

Produkt 1

HCID 10521779HCID 10521779, VerbindungAusbeute 13,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysator
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A mixture of 1-[2-(methylethoxy)phenyl]piperazine (IPP, 7.28 g, 0.033 mol), 3-acetylbenzonitrile (4.80 g, 0.033 mol), and titanium isopropoxide (11.74 g, 0.041 mol) was stirred at room temperature for 2 h, heated to 80° C. for several minutes, and then cooled to room temperature. Methanol (150 mL) was added and the mixture was heated to dissolve most of the solids. After cooling to room temperature, sodium borohydride (2.27 g, 0.060 mol) was added in portions and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated on a rotary evaporator and the residue was partitioned between 3N NaOH/CH2Cl2. The organic layer was separated, dried (K2CO3), filtered, and evaporated to an oily residue which was passed through flash grade silica using 4:1 hexane:EtOAc as eluant to give 3-[1-[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]ethyl]benzonitrile as an oil (1.55 g, 13.5%).

Aufarbeitung

  1. temperatureheated to 80° C. for several minutes
  2. temperaturecooled to room temperature
  3. temperaturethe mixture was heated
  4. dissolutionto dissolve most of the solids
  5. temperatureAfter cooling to room temperature
  6. stirringthe mixture was stirred overnight at room temperature
  7. concentrationThe reaction mixture was concentrated on a rotary evaporator
  8. customthe residue was partitioned between 3N NaOH/CH2Cl2
  9. customThe organic layer was separated
  10. dry with materialdried (K2CO3)
  11. filtrationfiltered
  12. customevaporated to an oily residue which

Quellen und Nachweise

ORD-Eintrag
ord-377eefd82ac446c19229c87403c1f00a
Quelldatensatz
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05569659

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