Chloroacetaldehyde → HCID 67064861, compound

To a solution of (trans)-2-(4-(4-bromobenzyloxy)phenyl)cyclopropanamine (4.2 g, 13.24 mmol) in DCM (42 mL) 4° A molecular sieves was added followed by chloroacetaldehyde (1.0 g, 13.24 mmol), stirred at RT for 1 h. After completion of reaction, monitored by TLC, the reaction mixture was cooled to −10° C. and Na(CN)BH3 (0.99 mg, 15.88 mmol) was added and stirred at RT for 2 h. After completion, the reaction mixture was quenched with NH4Cl (5%) and filtered through a pad of celite. The filtrate was extracted with DCM (2×150 mL) combined extracts were washed with water (50 mL), dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography by using EtOAc: Pet ether to get (trans)-2-(4-(4-bromobenzyloxy)phenyl)-N-(2-chloroethyl)cyclopropanamine (4 g, 80%)

1. customAfter completion of reaction
2. temperaturethe reaction mixture was cooled to −10° C.
3. stirringstirred at RT for 2 h
4. customAfter completion, the reaction mixture was quenched with NH4Cl (5%)
5. filtrationfiltered through a pad of celite
6. extractionThe filtrate was extracted with DCM (2×150 mL)
7. washwere washed with water (50 mL)
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. customevaporated
11. customThe residue was purified by flash column chromatography

ORD record

ord-890e0b39e0de43cdb04ab710a10bf3ed

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859555B2