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

Temperature

70 °C

Allylamine (29.5 ml, 392.5 mmol) was warmed to 40° C. under nitrogen atmosphere. Chloromethyltrimethylsilane (25.0 ml, 180 mmol) was added very slowly to the allylamine while stirring. After the addition was complete the mixture was warmed to 70° C. for 24 hours. The mixture was cooled to 0° C. and water (25 ml) was added, followed by 2 N NaOH solution (75 ml). The mixture was stirred for one hour and was then extracted with tert-butyl methyl ether (tBME; 2×100 ml). The organic layer was dried with Na2SO4 and then concentrated under vacuum at 300 mbar at 70° C. to give pure N-((trimethylsilyl)methyl)prop-2-en-1-amine (21 g, 146.5 mmol) in 81% c.y.

1. additionAfter the addition
2. temperatureThe mixture was cooled to 0° C.
3. stirringThe mixture was stirred for one hour
4. extractionwas then extracted with tert-butyl methyl ether (tBME; 2×100 ml)
5. dry with materialThe organic layer was dried with Na2SO4
6. concentrationconcentrated under vacuum at 300 mbar at 70° C.

ORD record

ord-a2a3022960dc45328e3304b28f3dc2ac

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964739B2