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

Participants

Reaction Conditions

Reaction Steps

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+).

Provenance & Evidence