Benzylamine → N-Benzylbut-3-en-1-amine

Temperature

75 °C

To a solution of benzylamine (100 mL, 0.9 mol) and 4-bromobut-1-ene (25 g, 0.18 mmol) in ethanol (250 mL) was added sodium iodide (1.0 g, 6.7 mmol). The reaction mixture was degassed via argon bubbling for 20 min then heated to 75° C. for 4 h. After cooling, the reaction mixture was diluted with dichloromethane (1 L) and 1M KOH (500 mL) was added. The two phases were separated and the aqueous layer was further extracted with dichloromethane (3×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (SiO2, ethyl acetate to 10:1 ethyl acetate/triethylamine) provided N-benzylbut-3-en-1-amine (24.5 g, 84%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.31-7.28 (m, 3H), 7.24-7.21 (m, 2H), 5.82-5.72 (m, 1H), 5.10-5.00 (m, 2H), 3.77 (s, 2H), 2.68 (t, J=6.8 Hz, 2H), 2.29-2.23 (m, 2H), 1.36 (br s, 1H).

1. customThe reaction mixture was degassed via argon bubbling for 20 min
2. temperatureAfter cooling
3. additionthe reaction mixture was diluted with dichloromethane (1 L) and 1M KOH (500 mL)
4. additionwas added
5. customThe two phases were separated
6. extractionthe aqueous layer was further extracted with dichloromethane (3×200 mL)
7. dry with materialThe combined organic layers were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification by flash chromatography (SiO2, ethyl acetate to 10:1 ethyl acetate/triethylamine)

ORD record

ord-cccb2a0a91254ae6880d46f6f646443d

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067949B2