Dicyclohexylcarbodiimide → 3-(3-Bromophenyl)propanamide

To a solution of 3-(3-bromophenyl)propionic acid (93) (5.0 g, 21.8 mmol) and N-hydroxysuccinimide (2.51 gr., 21.8 mmole) in CH2Cl2 (100 ml) was added dicyclohexylcarbodiimide (4.50 g, 21.8 mmol) and the mixture was stirred at room temperature for 45 min. The precipitate was removed by filtration and the filtrate was cooled in an ice bath. Ammonia gas was bubbled into the solution for 2 min then allowed to warm to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to an oil which was triturated with hexanes. The product was collected by filtration to give 3-(3-bromophenyl)propionamide (94) as a white solid. This material was taken on to the next synthetic step without further purification. Yield (4.62 g, 93%): 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H).

1. customThe precipitate was removed by filtration
2. temperaturethe filtrate was cooled in an ice bath
3. customAmmonia gas was bubbled into the solution for 2 min
4. temperatureto warm to room temperature overnight
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. dissolutionthe residue was dissolved in EtOAc
7. washThis solution was washed with saturated aqueous NaHCO3 and brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated under reduced pressure to an oil which
10. customwas triturated with hexanes
11. filtrationThe product was collected by filtration

ORD record

ord-3d9ccc428e2b4968b253a57903decff1

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653142B2