Benzylamine → N-benzyl-4-methylaniline

HRID 382086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382086
CC([O-])(C)C.[Na+].Cl[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:15]([NH:22][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 3

HCID 7504BenzylamineHCID 78104-ChlorotolueneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 79403N-benzyl-4-methylanilineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 634876Binap, (A+-)-KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

An oven dried Schlenk tube was purged with argon and charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1.0 mol % Pd), Cy-BINAP (9.6 mg, 0.015 mmol, 1.5 mol %), and NaOtBu (135 mg, 1.4 mmol). The tube was purged with argon and charged with toluene (2 mL), 4-chlorotoluene (0.12 mL, 1.0 mmol), and benzylamine (0.165 mL, 1.5 mmol). The mixture was heated to 100° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was cooled to room temperature, diluted with ether (20 mL), filtered through celite, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 177 mg (90%) of a pale yellow oil.

Aufarbeitung

  1. customAn oven dried Schlenk tube
  2. customwas purged with argon
  3. customThe tube was purged with argon
  4. customhad been completely consumed
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additiondiluted with ether (20 mL)
  7. filtrationfiltered through celite
  8. concentrationconcentrated in vacuo
  9. customThe crude material was then purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9153d6751a1d4485a028ceb3b481e1e0
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307087B1

Notizen zur Reaktion

Wird geladen…