Isopropylamine → N-[(2-Bromopyridin-4-yl)methyl]propan-2-amine

After a mixture of isopropylamine (2.8 mL), 2-bromopyridine-4-carboxaldehyde (3.00 g), and chloroform (60 mL) was stirred at room temperature, sodium triacetoxyborohydride (10.00 g) was added thereto and the mixture was stirred for 21 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the resulting mixture was then stirred for a while and extracted with chloroform. The organic phase was separated out and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=88:12-0:100) and (NH silica gel cartridge, hexane:ethyl acetate=90:10-0:100) to afford the title compound (2.64 g).

1. stirringthe mixture was stirred for 21 hr
2. stirringthe resulting mixture was then stirred for a while
3. extractionextracted with chloroform
4. customThe organic phase was separated out
5. distillationthe solvent was distilled off under reduced pressure
6. customThe resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=88:12-0:100) and (NH silica gel cartridge, hexane:ethyl acetate=90:10-0:100)

ORD record

ord-5846bd16d3c644b6aeb1132c4549306e

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729271B2