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Ethanol → 2-Methyl-5-phenylbenzylamine

HRID 1883638
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1883638
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].C(O)C.O.N>O1CCOCC1.[Ni].O>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH2:4][NH2:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 702Ethanol2×HCID 111715372-Methyl-5-phenylbenzonitrileHCID 12896473Azane;hydrate2×

Produkt 1

HCID 235082132-Methyl-5-phenylbenzylamineAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysator2×
HCID 962
Water
Lösungsmittel
2×
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4.46 g (23.1 mmol) of 2-methyl-5-phenylbenzonitrile was dissolved in 26 ml of 1,4-dioxane and to this was added 5 ml of ethanol. To this solution was added 9 ml of 28 wt % ammonia water, and 3 g of a suspension of Raney nickel W2 (manufactured by Aldrich; 50 wt % in water). This mixture was stirred for 8 hours at room temperature under hydrogen atmosphere. To this mixture was further added 2 g of a suspension of Raney nickel W2 (manufactured by Aldrich; 50 wt % in water), 8 ml of 28 wt % ammonia water and 20 ml of ethanol, and the mixture was stirred for 4.5 hours at room temperature under hydrogen atmosphere. The reaction mixed was filtrated through celite, and the filtrate was concentrated. The residue was distilled by using Kugelrohl distillation apparatus (0.5 mmHg, set temperature: 216° C.), to obtain 4.25 g of 2-methyl-5-phenylbenzylamine.

Aufarbeitung

  1. stirringthe mixture was stirred for 4.5 hours at room temperature under hydrogen atmosphere
  2. additionThe reaction mixed
  3. filtrationwas filtrated through celite
  4. concentrationthe filtrate was concentrated
  5. distillationThe residue was distilled
  6. distillationKugelrohl distillation apparatus (0.5 mmHg, set temperature: 216° C.)

Quellen und Nachweise

ORD-Eintrag
ord-516c299f5876434a91b32d53289176b2
Quelldatensatz
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06762197B2

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