Hydrochloric Acid → (1R,2S)-2-(4-Bromophenyl)cyclopropan-1-amine

Zn dust (1.97 g, 30 mol) was added in small portions, over a period of 30 min, to a vigorously stirred solution of 1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene (Intermediate A, 0.73 g, 3.0 mmol) in i-PrOH (25 mL) and HCl (11 mL of aqueous solution 2.7 N, 30 mmol). After 17 h the mixture was filtered through a pad of celite, that was washed with 10 mL of methanol. The filtrate was concentrated and 10 mL of water were added, washing with CH2Cl2 (3×15 mL). The organic layers were dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2) affording 0.06 g of (trans)-2-(4-bromophenyl)cyclopropanamine [white solid. 10% yield].

1. filtrationAfter 17 h the mixture was filtered through a pad of celite, that
2. washwas washed with 10 mL of methanol
3. concentrationThe filtrate was concentrated
4. addition10 mL of water were added
5. washwashing with CH2Cl2 (3×15 mL)
6. dry with materialThe organic layers were dried over anhydrous Na2SO4
7. filtrationfiltered
8. customAfter removal of the solvent
9. customthe crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2)

ORD record

ord-435eb13c993a453a92f529f1233e7acf

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946296B2