Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine
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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °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 and 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 afford the title compound as a clear liquid. 1H NMR (CDCl3) δ0.0 (s, 9H), 1.1 (br s, 1H), 2.01 (s, 2H), 3.76 (s, 2H), 7.1-7.3 (m, 5H).
Workup
- extractionthe product was extracted with 3×200 mL of diethyl ether
- washThe combined organic phase was washed with 100 mL of water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- distillationThe product was distilled at 115°-125° C.
Sources & evidence
- ORD record
- ord-89363de4ef9c45599aac39de098c2e06
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04994486
Reaction notes
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