Triethylamine → 3'-(N-Cyclopropylaminomethyl)acetophenone

Cyclopropylamine (5.71 g; 10.0 mmol) and triethylamine (1.01 g; 10.0 mmol) were dissolved in methanol (50 ml). While the mixture was stirred in an ice bath, 3′-bromomethylacetophenone (2.13 g; 10.0 mmol) in methanol (10 ml) was added dropwise. The mixture was removed from the ice bath, and stirred for 18 hours at room temperature. The solvent was evaporated under reduced pressure, and the residue was taken up in 2N hydrochloric acid (100 ml), followed by extraction with diethyl ether (100 ml). The aqueous layer was alkalinized with aqueous sodium hydroxide solution, and the mixture was extracted with chloroform (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→0:1), to thereby yield 0.66 g of the target compound as yellow oily matter (yield: 34.9%).

1. customThe mixture was removed from the ice bath
2. stirringstirred for 18 hours at room temperature
3. customThe solvent was evaporated under reduced pressure
4. extractionfollowed by extraction with diethyl ether (100 ml)
5. extractionthe mixture was extracted with chloroform (100 ml)
6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→0:1)

ORD record

ord-b731049b1b774a9eb9258e4e858a1c0a

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586633B1