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

Triethylamine → 4-(cis-3,5-Dimethyl-1-piperazinyl)-2-nitrobenzonitrile

HRID 130415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 130415
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.C[O-].[Na+].C(N(CC)CC)C.[CH3:23][C@H:24]1[CH2:29][NH:28][CH2:27][C@@H:26]([CH3:30])[NH:25]1>CC(O)=O.CC(P(C(C)(C)C)C1C(C2[C-]=CC=CC=2)=CC=CC=1)(C)C.[Pd]>[CH3:23][C@H:24]1[NH:25][C@@H:26]([CH3:30])[CH2:27][N:28]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=2)[CH2:29]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 969244-Chloro-2-nitrobenzonitrileHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 10942334Sodium Methoxide

Produkt 1

HCID 691981564-(cis-3,5-Dimethyl-1-piperazinyl)-2-nitrobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11982262
2-(2'-Di-tert-butylphosphine)biphenylpalladium(II) acetate
Katalysator

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-chloro-2-nitrobenzonitrile (Tetrahedron 1994, 50, 5515-5126) (650 mg, 3.56 mmol), sodium methoxide (270 mg, 5.00 mmol) and acetato-(2′-di-tert-butylphosphino-1,1′-biphenyl-2-yl)palladium (II) (115 mg, 0.25 mmol) was treated with triethylamine (0.25 ml, 1.79 mmol) followed by cis-2,6-dimethylpiperazine (488 mg, 4.27 mmol) and the mixture heated to 85° C. under an inert atmosphere over 30 minutes. The mixture was then kept at this temperature for 16 hours. The mixture was then filtered through kieselguhr, washing with toluene (50 ml) and the filtrate reduced in vacuo. The residue was then purified using an SCX ion exchange cartridge (Varian bond-elute) eluting with methanol followed by 2M ammonia in methanol to afford a dark residue which was purified by mass directed autoprep BPLC to afford the title compound as the formic acid salt. MS (ES+) m/e 261 [M+H]+.

Aufarbeitung

  1. filtrationThe mixture was then filtered through kieselguhr
  2. washwashing with toluene (50 ml)
  3. customThe residue was then purified
  4. washan SCX ion exchange cartridge (Varian bond-elute)
  5. washeluting with methanol
  6. customto afford a dark residue which
  7. customwas purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-c9f26323c77a4bdebefe7106d812054a
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07381728B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion