3-(3-Bromophenyl)propanamide → 3-(3-Bromophenyl)propan-1-amine

To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 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 reaction was quenched with the cautious addition of 6 M HCl to pH 1
2. stirringAfter stirring 4 h the solution
3. additionwas adjusted to pH>10 with the addition of 50% aqueous NaOH
4. extractionThis aqueous solution was extracted with EtOAc
5. washThe combined organics were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-08a834a0b0fe46a48ef40c9076665ca6

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08653142B2