Borane → 3-(2-Bromophenyl)-1-propanamine

Into a 250-mL 3-necked round-bottom flask, was placed a solution of 3-(2-bromophenyl)propanenitrile (2.1 g, 10.00 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of borane (1 mol/L in THF, 50 mL, 5.00 equiv) dropwise with stiffing at 0° C. The resulting solution was stirred for overnight at room temperature. The reaction was then quenched by the addition of 50 mL of water at 0° C. and extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride. The aqueous solution was extracted with 30 mL of ethyl acetate and the aqueous layers were combined. The pH value of the aqueous solution was adjusted to 10 with 10% aqueous sodium hydroxide. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, concentrated under vacuum. This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil.

1. customInto a 250-mL 3-necked round-bottom flask, was placed
2. customwith stiffing at 0° C
3. customThe reaction was then quenched by the addition of 50 mL of water at 0° C.
4. extractionextracted with 3×50 mL of ethyl acetate
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. dissolutionThe residue was dissolved in 30 mL of 6N aqueous hydrogen chloride
8. extractionThe aqueous solution was extracted with 30 mL of ethyl acetate
9. extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under vacuum
12. customThis resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil

ORD record

ord-79d238cbbba346d49491bc1c478c6888

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193693B2