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 portionwise. The aqueous solution was extracted with EtOAc (3×) and the organic solution was dried (MgSO4), filtered, and concentrated. The product (4.01 g) was used in the next step without further purification. 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 portionwise
10. extractionThe aqueous solution was extracted with EtOAc (3×)
11. dry with materialthe organic solution was dried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated
14. customThe product (4.01 g) was used in the next step without further purification

ORD record

ord-75480841508f445aa549d56f4b004fcc

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06288120B1