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

To a solution of (E)-N-benzylidenebut-3-en-1-amine (1.298 gm, 8.15 mmol) in EtOH (25 mL) cooled to 0° C. was added NaBH4 (0.324 g, 8.56 mmol) portionwise over 40 min. After addition, the reaction mixture was stirred at rt for 3 hr. The reaction mixture was filtered and the filtrate was concentrated to give a white semi-solid residue. To the residue 50 mL of DCM was added. The resulting milky solution was stirred for 15 min and then was filtered. The obtained clear filtrate was concentrated to give N-benzylbut-3-en-1-amine (1.30 g, 6.85 mmol, 84% yield) as a pale yellow oil. Anal. Calcd. for C11H15N m/z 161.2. found: 162.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.42-7.21 (m, 5H), 5.79 (ddt, J=17.1, 10.2, 6.9 Hz, 1H), 5.13-4.99 (m, 2H), 3.80 (d, J=6.8 Hz, 2H), 3.29 (q, J=6.8 Hz, 1H), 2.71 (q, J=6.9 Hz, 1H), 2.29 (q, J=6.8 Hz, 1H), 1.25 (dt, J=9.1, 7.1 Hz, 1H), 1.12-1.03 (m, 1H).

1. additionAfter addition
2. filtrationThe reaction mixture was filtered
3. concentrationthe filtrate was concentrated
4. customto give a white semi-solid residue
5. stirringThe resulting milky solution was stirred for 15 min
6. filtrationwas filtered
7. concentrationThe obtained clear filtrate was concentrated

ORD record

ord-cf25fe073b414ea3bce041611541a292

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346852B2