Hydrochloric Acid → 2-(3,5-Dichlorophenyl)ethan-1-amine

2-(3,5-dichlorophenyl)acetonitrile (155.5 mg, 0.836 mmol), 0.3 molar in THF, was heated to reflux and then treated with Borane-methyl sulfide complex (87.20 μL, 0.919 mmol). After 1 hour of refluxing, the reaction mixture was cooled to ambient temperature and then treated dropwise with 5.0 molar hydrochloric acid (601.8 μl, 3.009 mmol). The reaction mixture was heated to reflux for an additional 30 minutes. After 30 minutes the reaction mixture was cooled to 0° C. and treated with 1.0 molar sodium hydroxide (4597 μL, 4.597 mmol). The reaction mixture was diluted with diethyl ether and partitioned with deionized water. The organic layer was dried with potassium carbonate 98% powder, filtered, concentrated, and dried for one minute under high vacuum to provide the title compound (135.2 mg, 0.7113 mmol, 85.1% yield) as a light yellow oil.

1. temperatureto reflux
2. additiontreated with Borane-methyl sulfide complex (87.20 μL, 0.919 mmol)
3. temperatureAfter 1 hour of refluxing
4. temperatureThe reaction mixture was heated
5. temperatureto reflux for an additional 30 minutes
6. temperatureAfter 30 minutes the reaction mixture was cooled to 0° C.
7. custompartitioned with deionized water
8. dry with materialThe organic layer was dried with potassium carbonate 98% powder
9. filtrationfiltered
10. concentrationconcentrated
11. customdried for one minute under high vacuum

ORD record

ord-5228bc9e8d77438981f6178892c99e74

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569522B2