ChemicalBook CAS DataBase List N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine synthesis

4synthesis methods

Product Name:N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
CAS Number:93102-05-7
Molecular formula:C13H23NOSi
Molecular Weight:237.41

most conveniently prepared by treatment of benzylamine with chloromethyltrimethylsilane followed by formaldehyde and methanol.Access to higher ether homologs is achieved by replacing methanol with the appropriate alcohol. An alternate procedure involves alkylation of lithium N-benzyltrimethylsilymethylamide with methoxymethyl chloride.

50-00-0 Synthesis

50-00-0
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53215-95-5 Synthesis

53215-95-5
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$11.00/1g

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

93102-05-7
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$6.00/1g

Yield:93102-05-7 97.5%

Reaction Conditions:

Stage #1: formaldehyd;N-(trimethylsilylmethyl)benzylamine in water at 0;
Stage #2: with potassium carbonate in water at 20; for 2 h;

Steps:

Intermediate P16: N-Benzyl-1 -methoxy-N-[(trimethylsilyl)methyl]methanamine

To the solution of formaldehyde (37%, 16.816 g, 207.19 mmol) at 0°C N-benzylo- 1 -(trimethylsilyl)methanamine (Intermediate P15, 28.588 g, 144.89 mmol) was added dropwise. To the mixture solid potassium carbonate (16.182 g, 115.91 mmol) was added and the whole was stirred at room temperature for 2 hours. Water (50 ml) was added and the mixture was extracted with diethyl ether (2 x 50 ml). Organic layer was washed with brine and dried over sodium sulphate. Solvent and drying agent were removed to obtain 33.551 g of the title product in the form of a yellow oil (yield 97.5%). ¹H NMR (300 MHz, CDCl₃): δ 7.35 - 7.18 (m, 5H), 3.99 (s, 2H), 3.75 (s, 2H), 3.22 (s, 3H), 2.18 (s, 2H), 0.13 (s, 9H).

References:

WO2014/24125,2014,A1 Location in patent:Page/Page column 24-25

67-56-1 Synthesis