Allylamine → N-((trimethylsilyl)methyl)prop-2-en-1-amine

Temperature

70 °C

To 118 mL (1.57 mol) of allylamine warmed at 40° C. in an inert atmosphere was very slowly added 100 mL (0.72 mol) of chloromethyl trimethylsilane (approximate rate of 1 mL/min). The reaction mixture was slowly warmed to 70° C. and stirred for 24 h. The reaction mixture was cooled to 0° C. and to it was added water to break tip the gel and then 300 mL of 2N NaOH solution. The reaction mixture was extracted with ether. The combined organic fractions were washed with 500 mL of sat'd NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by distillation (bp 80-84° C. @ 100 torr) to give 75 g of the title compound.

1. temperatureThe reaction mixture was cooled to 0° C. and to it
2. extractionThe reaction mixture was extracted with ether
3. washThe combined organic fractions were washed with 500 mL of sat'd NaCl solution
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate was concentrated
7. distillationThe residue was purified by distillation (bp 80-84° C. @ 100 torr)

ORD record

ord-ca9dd621e3b44ab4a87f09928c84883d

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303593B1