Isoamylamine → (4-Bromo-2-chloro-benzyl)-(3-methyl-butyl)-amine

4-bromo-2-chloro-benzaldehyde (I-3a: 10.0 g, 46.0 mmol) was dissolved in methanol and treated with isoamylamine (4.78 g, 54.7 mmol). After stirring overnight at room temperature, sodium borohydride (5.2 g, 138 mmol) was added to the reaction mixture. After stirring for 1 hour at room temperature, the reaction mixture was quenched using concentrated (37%) hydrochloric acid and the volatiles were removed under reduced pressure. The residue was taken up in an aqueous 2 N sodium hydroxide solution and extracted with ethyl acetate (2 times). The combined organic phases were washed with a saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title product (I-3b: 12.7 g)

1. stirringAfter stirring for 1 hour at room temperature
2. customthe reaction mixture was quenched
3. concentrationusing concentrated (37%) hydrochloric acid
4. customthe volatiles were removed under reduced pressure
5. extractionextracted with ethyl acetate (2 times)
6. washThe combined organic phases were washed with a saturated aqueous sodium bicarbonate solution
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-3091268a30c3421598847dc60ee415d1

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07615651B2