Hydrochloric Acid → (trans)-2-(4-((2-Methoxyethoxy)methoxy)phenyl)cyclopropanamine

Zn dust (0.99 g, 15.1 mol) was added in small portions, over a period of 20 min, to a vigorously stirred solution of 1-((2-methoxyethoxy)methoxy)-4-((trans)-2-nitrocyclopropyl)benzene (Intermediate K, 0.40 g, 1.51 mmol) in i-PrOH (15 mL) and HCl (5.6 mL of 2.7 N aqueous solution, 15.1 mmol). After 16 h, the mixture was basified with NaOH (10% aqueous solution, 10 mL) and filtered through a pad of celite, that was washed with 10 mL of methanol. The filtrate was concentrated and 15 mL of water were added, extracting with CH2Cl2 (3×15 mL); the organic layers were washed with brine (25 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the crude product was purified by column chromatography on silica gel (2-5% MeOH/CH2Cl2) affording 0.26 g of (trans)-2-(4-((2-methoxyethoxy)methoxy)phenyl)cyclopropanamine [Rf=0.1 (5% MeOH/CH2Cl2), white solid, 73% yield].

1. filtrationfiltered through a pad of celite, that
2. washwas washed with 10 mL of methanol
3. concentrationThe filtrate was concentrated
4. addition15 mL of water were added
5. extractionextracting with CH2Cl2 (3×15 mL)
6. washthe organic layers were washed with brine (25 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. customAfter removal of the solvent
10. customthe crude product was purified by column chromatography on silica gel (2-5% MeOH/CH2Cl2)

ORD record

ord-cb30949c5aa24644be487a2ba28cc8de

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722743B2