Ammonia → 2-(3-chlorophenyl)-2-methylpropan-1-amine

Temperature

0 °C

To a solution of 2-(3-chloro-phenyl)-2-methyl-propionitrile (6.4 g, 35.7 mmol) in THF (80 mL) was added borane-tetrahydrofuran complex solution (71.3 mL, 71.3 mmol), and the resulting mixture was heated to reflux for 5 hours. After cooling to 0° C., aq. HCl (2 M, 10 mL) was added dropwise to quench the reaction. The mixture was then concentrated in vacuo to afford a solid residue, which was treated with aq. ammonia solution (6M in H2O). After extraction with ethyl acetate, the organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel, 180 g, 5% methanol in dichloromethane) to yield the title compound as oil (2.8 g, 43%). MS: 184.1 (M+H+).

1. temperaturethe resulting mixture was heated
2. temperatureto reflux for 5 hours
3. customto quench
4. customthe reaction
5. concentrationThe mixture was then concentrated in vacuo
6. customto afford a solid residue, which
7. extractionAfter extraction with ethyl acetate
8. customthe organic layer was dried over anhy
9. filtrationNa2SO4, filtered
10. concentrationconcentrated in vacuo
11. customThe crude product was purified by flash column chromatography (silica gel, 180 g, 5% methanol in dichloromethane)

ORD record

ord-3f20fdaf74ab4b3f9d5bfd30a905f573

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133158B2