Bis(2-chloroethyl)amine hydrochloride → 1-(2-Cyclohept-1-enylphenyl)piperazine

Temperature

200 °C

To a solution of 2-cyclohept-1-enylphenylamine (617 mg, 3.29 mmol) in 1,2-dichlorobenzene (8 mL) was added bis(2-chloroethyl)amine hydrochloride (705 mg, 3.95 mmol), and the mixture was stirred at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was blown into the reactor to remove the hydrogen chloride gas in the reactor. This procedure was repeated several times. After 5 hours, the reaction mixture was air-cooled to room temperature, and then aqueous solution of potassium carbonate, ethyl acetate and methanol were added to the reaction mixture and extraction was performed three times with ethyl acetate. The obtained organic layers were dried over anhydrous sodium sulfate, and then the desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 387 mg of the title compound as a brown oil.

1. customDuring the reaction
2. customto remove the hydrogen chloride gas in the reactor
3. temperaturethe reaction mixture was air-cooled to room temperature
4. additionaqueous solution of potassium carbonate, ethyl acetate and methanol were added to the reaction mixture and extraction
5. dry with materialThe obtained organic layers were dried over anhydrous sodium sulfate
6. filtrationthe desiccant was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

ORD record

ord-dfb0e43c67b4425f95afc2b6765cce39

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07425554B2