Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

HRID 1089031Notes

Reaction equation

HRID 1089031 reaction equation
[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]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 353458N-[(Trimethylsilyl)methyl]benzylamineYield 81.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
200 °C

Procedure

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-trimethysilylmethyl benzylamine as a clear liquid. 1H NMR (CDCl3) delta 0.0 (s, 9H), 1.1 (br s, 1H), 2.01 (s, 2H), 3.76 (s, 2H), 7.1-7.3 (m, 5H).

Workup

  1. temperaturethen cooled to 10° C
  2. extractionthe product was extracted with 3×200 mL of diethyl ether
  3. washThe combined organic phase was washed with 100 mL of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. distillationThe product was distilled at 115°-125° C.

Sources & evidence

ORD record
ord-52bef2d09289461cabe54e2db90b5b75
Source dataset
uspto-grants-1990_10
Patent number
US04963568

Reaction notes

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