Styrene Oxide → 2-allylamino-1-phenyl-ethanol

Temperature

100 °C

To a solution of 0.57 ml (5 mmol) 2-phenyl-oxirane in 5 ml tetrahydrofuran 0.26 g (1 mmol) magnesium bromide diethyl etherate was added at room temperature. The mixture was treated under argon with stirring with 0.56 ml (7.5 mmol) allylamine whereby a white suspension formed which dissolved after heating to 100° C. in a closed container. The yellow solution was heated at 100° C. for 2 hours, cooled to room temperature and stirred vigorously with 5 ml of 5N aqueous ammonium chloride solution for 10 minutes. The organic phase was separated, dried over 3 g of sodium sulfate, filtered and evaporated in a rotary evaporator. The oily residue containing the products was separated by chromatography on a silica gel column using tert.-butyl methyl ether containing 1% of conc. aqueous ammonia as the eluent to obtain 0.3 g of 2-allylamino-1-phenyl-ethanol (compound A) and 0.2 g 2-allylamino-2-phenyl-ethanol (compound B) as yellowish oils.

1. additionThe mixture was treated under argon
2. customformed which
3. dissolutiondissolved
4. temperatureThe yellow solution was heated at 100° C. for 2 hours
5. temperaturecooled to room temperature
6. customThe organic phase was separated
7. dry with materialdried over 3 g of sodium sulfate
8. filtrationfiltered
9. customevaporated in a rotary evaporator
10. additionThe oily residue containing the products
11. customwas separated by chromatography on a silica gel column

ORD record

ord-cc7d57be86eb41c281c476db7c9f0f2d

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437171B1