4-Butylbenzonitrile → 4-Butylbenzylamine

A solution of 4-butylbenzonitrile (3.63 g, 22.8 mmol) in THF (10 mL) was placed in a three-neck round bottom flask equipped with a Vigreux column and short-path distillation head. The solution was heated to reflux and BH3-methyl sulfide complex (2.0 M in THF, 15 mL, 30 mmol) was added dropwise over 15 minutes. Methyl sulfide was distilled off from the reaction mixture over 1 h and the solution was cooled to room temperature. Aqueous HCl (6N, 25 mL) was added slowly via an addition funnel and the mixture was heated at reflux for 30 minutes. The reaction was cooled to 0° C. and NaOH (7.0 g) was added protionwise. The aqueous solution was washed with EtOAc (3×) and the organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound of Method A (4.01 g). 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 2H), 7.24 (m, 2H), 4.04 (s, 2H), 2.62 (t, 2H), 1.58 (m, 2H), 1.34 (m, 2H), 0.92 (t, 3H).

1. customequipped with a Vigreux column and short-path distillation head
2. temperatureThe solution was heated
3. temperatureto reflux
4. distillationMethyl sulfide was distilled off from the reaction mixture over 1 h
5. additionAqueous HCl (6N, 25 mL) was added slowly via an addition funnel
6. temperaturethe mixture was heated
7. temperatureat reflux for 30 minutes
8. temperatureThe reaction was cooled to 0° C.
9. additionNaOH (7.0 g) was added protionwise
10. washThe aqueous solution was washed with EtOAc (3×)
11. dry with materialthe organic solution was dried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-cbdd3db73f22426aaaf7a97f98e8ea52

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06498172B1