Tert-Butylamine → N-(1,1-Dimethylethyl)benzenamine

HRID 41654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41654
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[Na+]>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].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([NH:5][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 6385Tert-ButylamineHCID 7961BromobenzeneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 254260N-(1,1-Dimethylethyl)benzenamineAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 634876Binap, (A+-)-KatalysatorHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of Pd(dba)2 (0.230 g, 0.400 mmol), (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene (0.374 g, 0.601 mmol) and toluene (40 mL) in a sealed tube was stirred for 30 min at room temperature before adding tert-butylamine (1.80 mL, 17.1 mmol), bromobenzene (1.60 mL, 15.2 mmol) and sodium tert-butoxide (2.01 g, 20.9 mmol). The reaction solution was flushed with Ar for 1 min. and was stirred for 24 h at 100° C. After cooling the reaction mixture to room temperature, Et2O (50 mL) was added. The reaction mixture was filtered through a pad of celite and was concentrated. Vacuum distillation of the crude mixture at 60° C. gave the desired product (1.876 g, 83.3%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) δ 7.17 (t, J=7.9 Hz, 2 H), 6.83-6.69 (m, 3H), 3.37 (br. s, 1H), 1.35 (s, 9H); 13C NMR (75 MHz, CDCl3) δ 147.1, 129.1, 118.6, 117.7, 51.7, 30.3. HRMS-ESI (m/z): [M+H]+ calcd for C10H15N, 150.1277. found, 150.1270.

Aufarbeitung

  1. customThe reaction solution was flushed with Ar for 1 min.
  2. stirringwas stirred for 24 h at 100° C
  3. temperatureAfter cooling the reaction mixture to room temperature
  4. additionEt2O (50 mL) was added
  5. filtrationThe reaction mixture was filtered through a pad of celite
  6. concentrationwas concentrated
  7. distillationVacuum distillation of the crude mixture at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-9f854e8153844d71b6e4efcc302cea08
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530687B2

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