Monomethylamine methanol → HCID 117987740, compound

To methyl 1-(4-bromophenyl)piperidine-4-carboxylate (950 mg) was added methylamine methanol solution (25%, 20 mL) at room temperature. The reaction mixture was stirred overnight at room temperature, and concentrated under reduced pressure. To a solution of the residue in acetonitrile (15 mL) were successively added tetraethylammonium bromide (1.05 g), isoamyl nitrite (1.05 g) and copper(I) bromide (0.09 g) at room temperature. The reaction mixture was stirred at room temperature for 40 min, and then at 60° C. for 2 hr. The reaction mixture was added to water, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (800 mg).

1. concentrationconcentrated under reduced pressure
2. customat room temperature
3. stirringThe reaction mixture was stirred at room temperature for 40 min
4. waitat 60° C. for 2 hr
5. additionThe reaction mixture was added to water
6. extractionthe mixture was extracted with diethyl ether
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

ORD record

ord-34cc83b333c643ea9fc5922b4bac03d1

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371320B2