Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 54148

Reaktionsgleichung

Reaktionsgleichung von HRID 54148
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12]>[OH-].[Na+]>[CH3:10][Si:11]([CH2:14][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 75361Silane, (chloromethyl)trimethyl-

Produkt 1

HCID 353458N-[(Trimethylsilyl)methyl]benzylamineAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A mixture of 264 mL (2.42 mol) of benzylamine and 97.7 g. (0.796 mol) of chloromethyltrimethylsilane was heated to 200° C. for 2.5 h then cooled to 10° C. A 0.1M sodium hydroxide solution (400 mL) was added and the product was extracted with 3×200 mL of diethyl ether. The combined organic phase was washed with 100 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product was distilled at 115°-125° C. and 5 mm of Hg to give 125.4 g (81% yield) of N-trimethylsilylmethyl benzylamine as a clear liquid; 1H NMR (CDCl3) δ: 0.0 (s, 9H), 1.1 (br s, 1H), 2.01 (s, 2H), 3.76 (s, 2H), 7.1-7.3 (m, 5H).

Aufarbeitung

  1. extractionthe product was extracted with 3×200 mL of diethyl ether
  2. washThe combined organic phase was washed with 100 mL of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. distillationThe product was distilled at 115°-125° C.

Quellen und Nachweise

ORD-Eintrag
ord-c91618267a6b4420a59188bf2a6f2187
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621133

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