Ammonium Hydroxide → 4-(Aminomethyl)benzonitrile

4-Cyano-benzyl bromide (4.00 g) was combined with 1,4-dioxane (2 mL) and conc. aq. ammonium hydroxide (30 mL). The reaction mixture was sealed with a teflon plug and stirred overnight at ambient temperature. The reaction mixture was concentrated to dryness in vacuo. The crude material consisted of a mixture of the desired mono- and undesired bis-benzyl adducts. The undesired product was removed by repeated precipitation from hot methanol, enriching the desired product in the filtrate. After three cycles, pure title compound was isolated as the hydrobromide salt (2.38 g).

1. concentrationThe reaction mixture was concentrated to dryness in vacuo
2. additionThe crude material consisted of a mixture of the desired mono- and undesired bis-benzyl adducts
3. customThe undesired product was removed
4. customprecipitation from hot methanol

ORD record

ord-765323f016c14bce891a9f39905f5587

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07250518B2