Hydrazine → HCID 15055857, compound

7.50 g (24.77 mmol) of 4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine and 6.92 g (27.24 mmol) of N-(2-bromoethyl)phthalimide were dissolved in 60 ml of dioxane, and 4.11 g (29.74 mmol) of potassium carbonate was added. The mixture was stirred at an oil bath temperature of 90° to 100° C. for 3 hours. After the reaction, the insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using a mixture of ethyl acetate and methanol in the volume ratio 25:1 as an eluent. The desired fraction was concentrated under reduced pressure, and 60 ml of ethanol and 1.61 g (32.16 mmol) of hydrazine (hydrate) were added to the residue, and the mixture was stirred under reflux. After 200 ml of 1N aqueous sodium hydroxide was added to the reaction mixture, the mixture was extracted twice with 200 ml of chloroform. The chloroform extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3.50 g (41%) of 2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethylamine as an oily product.

1. customAfter the reaction
2. filtrationthe insolubles were filtered off
3. concentrationthe filtrate was concentrated under reduced pressure
4. customThe residue was separated by silica gel column chromatography
5. additiona mixture of ethyl acetate and methanol in the volume ratio 25:1 as an eluent
6. additionwere added to the residue
7. stirringthe mixture was stirred
8. temperatureunder reflux
9. extractionthe mixture was extracted twice with 200 ml of chloroform
10. extractionThe chloroform extract
11. dry with materialwas dried over anhydrous sodium sulfate
12. concentrationconcentrated under reduced pressure

ORD record

ord-c476f6c0deb44775ab78a4283595b55a

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04929618