Allylamine → N-(3-phenylallyl)-allylamine

A solution of cinnamyl bromide (10 g, 50.7 mmol) in 250 mL tetrahydrofuran was added dropwise to a solution of allyl amine (38 ml, 507 mmol) in 50 mL tetrahydrofuran at 0° C. the mixture was allowed to slowly come to room temperature then stirred 20 hours. The tetrahydrofuran was removed in-vacuo, and the residue was partitioned between 500 mL of ethyl acetate and 200 ml of water. The layers were separated, the organic phase was washed with water followed by brine, then dried over sodium sulfate and concentrated to an amber oil. The oil was purified by flash chromatography on an 8×15 cm silica column, eluting with 5% methanol/chloroform followed by 10% methanol/chloroform. Obtained 7.2 g of an amber oil as product. Yield=81%. NMR (300 MHz, CDCl3) δ7.39-7.20 (m, 5H), 6.54 (d, 1H, J=16 Hz), 6.35-6.26 (m, 1H), 6.01-5.87 (m, 1H), 5.24-5.14 (m, 2H), 3.43 (d, 2H, J=7 Hz), 3.31 (d, 2H, J=6 Hz).

1. customto slowly come to room temperature
2. customThe tetrahydrofuran was removed in-vacuo
3. customthe residue was partitioned between 500 mL of ethyl acetate and 200 ml of water
4. customThe layers were separated
5. washthe organic phase was washed with water
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated to an amber oil
8. customThe oil was purified by flash chromatography on an 8×15 cm silica column
9. washeluting with 5% methanol/chloroform

ORD record

ord-14362707fb914000a7e04c9ae45c38fb

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06784200B2